Compound, organic electroluminescent material, organic electroluminescent element, and electronic apparatus

ABSTRACT

A compound represented by formula (1): 
                         
wherein Ar is a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted nitrogen-comprising heteroaryl group having 5 to 30 ring atoms; each of L 1  and L 2  is independently a single bond, a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heteroarylene group having 5 to 30 ring atoms, or a substituted or unsubstituted divalent linking group wherein 2 to 4 groups selected from an arylene group having 6 to 30 ring carbon atoms and a heteroarylene group having 5 to 30 ring atoms are bonded to each other via a single bond; A is a monovalent group represented by formula (2); and B is a monovalent group represented by formula (5):
 
                         
wherein R 1  to R 10  and R 21  to R 30  are as defined in the description, enables the emission of light of a purer blue (shorter wavelength), a narrower half width (higher color purity), and a single peak with no second peak.

TECHNICAL FIELD

The present invention relates to compounds, materials for organicelectroluminescence devices, organic electroluminescence devices, andelectronic devices.

BACKGROUND ART

Recently, organic electroluminescence devices (organic EL devices) havebeen used in wide applications, such as an emission device for mobiledisplays. As a blue fluorescent emitting component, i.e. a blue emittingmaterial (blue dopant material) for use in such applications, a diaminecompound of a fused aryl ring has been hitherto mainly developed.Particularly, a diaminopyrene dopant has been known to have a high colorpurity.

In the application to display, it has been required to further improvethe color purity to obtain a high color reproducibility, this in turnrequiring an emission of light with shorter wavelength. PatentLiteratures 1 to 5 propose fluorene compounds as materials which realizethe emission of light with a shorter wavelength.

CITATION LIST Patent Literature

-   Patent Literature 1: JP 2008-115093A-   Patent Literature 2: WO2014/069602-   Patent Literature 3: WO2008/006449-   Patent Literature 4: WO2014/037077-   Patent Literature 5: WO2014/106522

SUMMARY OF INVENTION Technical Problem

However, known fluorene compounds provide, in many cases, an emissionspectrum having a broad peak with a large half width or having a peakwith a second peak. In view of optical design of device, a materialwhich provides an emission spectrum having no second peak and a smallhalf width has been required in the application to display.

In an aspect, the present invention provides a material which enablesthe emission of light of a purer blue (shorter wavelength), a narrowerhalf width (higher color purity), and more suitable spectrum (singlepeak without second peak), as compared with the emission of lightobtained by the emitting materials described in Patent Literature 1 to5. In another aspect, the present invention provides a material fororganic EL device comprising the compound and an organic EL devicecomprising the compound. In still another aspect, the present inventionprovides an electronic device comprising the organic EL device.

Solution to Problem

The inventors have found that a compound comprising the specific fusedfluorene structure represented by formula (1) as the main skeleton,wherein one monocyclic ring is fused to each of two benzene rings of thefluorene structure, enables the emission of light of a purer blue(shorter wavelength), a narrower half width (higher color purity), andmore suitable spectrum (single peak with no second peak). The presentinvention has been made on the basis of this finding.

In an aspect of the invention, the compound represented by formula (1)is provided:

wherein:

Ar is a substituted or unsubstituted alkyl group having 1 to 20 carbonatoms, a substituted or unsubstituted aryl group having 6 to 30 ringcarbon atoms, or a substituted or unsubstituted nitrogen-comprisingheteroaryl group having 5 to 30 ring atoms;

each of L₁ and L₂ is independently a single bond, a substituted orunsubstituted arylene group having 6 to 30 ring carbon atoms, asubstituted or unsubstituted heteroarylene group having 5 to 30 ringatoms, or a substituted or unsubstituted divalent linking group, wherein2 to 4 groups selected from an arylene group having 6 to 30 ring carbonatoms and a heteroarylene group having 5 to 30 ring atoms are bonded toeach other via a single bond;

A is a monovalent group represented by formula (2):

wherein:

each of R₁ and R₂ is independently a hydrogen atom, a substituted orunsubstituted alkyl group having 1 to 20 carbon atoms; a mono-, di-, ortrialkylsilyl group each comprising a substituted or unsubstituted alkylgroup having 1 to 20 carbon atoms; a substituted or unsubstituted arylgroup having 6 to 30 ring carbon atoms; a mono-, di-, or triarylsilylgroup each comprising a substituted or unsubstituted aryl group having 6to 30 ring carbon atoms; or a substituted or unsubstituted heteroarylgroup having 5 to 30 ring atoms; wherein R₁ and R₂ may be bonded to eachother to form a ring;

adjacent two groups in one pair selected from R₈ and R₄, R₄ and R₅, andR₅ and R₆ are bonded to each other to form a divalent group representedby formula (3);

adjacent two groups in one pair selected from R₇ and R₈, R₈ and R₉, andR₉ and R₁₀ are bonded to each other to form a divalent group representedby formula (4);

wherein:

each of R₁₁ to R₁₈ is independently a hydrogen atom; a substituted orunsubstituted alkyl group having 1 to 20 carbon atoms; a mono-, di-, ortrialkylsilyl group each comprising a substituted or unsubstituted alkylgroup having 1 to 20 carbon atoms; a substituted or unsubstituted arylgroup having 6 to 30 ring carbon atoms; a mono-, di-, or triarylsilylgroup each comprising a substituted or unsubstituted aryl group having 6to 30 ring carbon atoms; or a substituted or unsubstituted heteroarylgroup having 5 to 30 ring atoms;

provided that one selected from R₃ to R₆ which do not form the divalentgroup represented by formula (3), R₇ to R₁₀ which do not form thedivalent group represented by formula (4), and R₁₁ to R₁₈ is a singlebond bonded to L₁;

each selected from R₃ to R₆ which do not form the divalent grouprepresented by formula (3) and is not a single bond bonded to L₁, andeach selected from R₇ to R₁₀ which do not form the divalent grouprepresented by formula (4) and is not a single bond bonded to L₁ isindependently a hydrogen atom; a substituted or unsubstituted alkylgroup having 1 to 20 carbon atoms; a mono-, di-, or trialkylsilyl groupeach comprising a substituted or unsubstituted alkyl group having 1 to20 carbon atoms; a substituted or unsubstituted aryl group having 6 to30 ring carbon atoms; a mono-, di-, or triarylsilyl group eachcomprising a substituted or unsubstituted aryl group having 6 to 30 ringcarbon atoms; or a substituted or unsubstituted heteroaryl group having5 to 30 ring atoms;

B is a monovalent group represented by formula (5):

wherein:

each of R₂₁ and R₂₂ is independently a hydrogen atom, a substituted orunsubstituted alkyl group having 1 to 20 carbon atoms, a mono-, di-, ortrialkylsilyl group each comprising a substituted or unsubstituted alkylgroup having 1 to 20 carbon atoms, a substituted or unsubstituted arylgroup having 6 to 30 ring carbon atoms, a mono-, di-, or triarylsilylgroup each comprising a substituted or unsubstituted aryl group having 6to 30 ring carbon atoms, or a substituted or unsubstituted heteroarylgroup having 5 to 30 ring atoms, wherein R₂₁ and R₂₂ may be bonded toeach other to form a ring;

each of R₂₃ to R₃₀ is independently a hydrogen atom, a substituted orunsubstituted alkyl group having 1 to 20 carbon atoms, a mono-, di-, ortrialkylsilyl group each comprising a substituted or unsubstituted alkylgroup having 1 to 20 carbon atoms, a substituted or unsubstituted arylgroup having 6 to 30 ring carbon atoms, a mono-, di-, or triarylsilylgroup each comprising a substituted or unsubstituted aryl group having 6to 30 ring carbon atoms, or a substituted or unsubstituted heteroarylgroup having 5 to 30 ring atoms;

adjacent groups in one or two pairs selected from R₂₃ and R₂₄, R₂₄ andR₂₅, and R₂₅ and R₂₆ may be bonded to each other to form a ring;

adjacent groups in one or two pairs selected from R₂₇ and R₂₈, R₂₈ andR₂₉, and R₂₉ and R₃₀ may be bonded to each other to form a carbon ring;

provided that one selected from R₂₇ to R₃₀ which do not form theoptional carbon ring is a single bond bonded to L₂, or one of ringcarbon atoms of the carbon ring which is optionally formed by one pairselected from R₂₇ and R₂₈, R₂₈ and R₂₉, and R₂₉ and R₃₀ is bonded to L₂;and

an optional substituent referred to by “substituted or unsubstituted” isselected from the group consisting of a substituted or unsubstitutedalkyl group having 1 to 20 carbon atoms; a mono-, di-, or trialkylsilylgroup each comprising a substituted or unsubstituted alkyl group having1 to 20 carbon atoms; a substituted or unsubstituted aryl group having 6to 30 ring carbon atoms; a mono-, di-, or triarylsilyl group eachcomprising a substituted or unsubstituted aryl group having 6 to 30 ringcarbon atoms; and a substituted or unsubstituted heteroaryl group having5 to 30 ring atoms.

In another aspect of the invention, a material for organicelectroluminescence device comprising the compound (1) is provided.

In still another aspect of the invention, an organic electroluminescencedevice is provided, which comprises a cathode, an anode, and at leastone organic thin film layer provided between the cathode and the anode,wherein the at least one organic thin film layer comprises a lightemitting layer and at least one layer of the at least one organic thinfilm layer comprises the compound (1).

In still another aspect of the invention, an electronic devicecomprising the organic electroluminescence device is provided.

Advantageous Effects of Invention

The compound (1) realizes the emission of light of a purer blue (shorterwavelength), a narrower half width (higher color purity), and a moresuitable spectrum (single peak with no second peak). In an aspect of theinvention, a material for organic EL device comprising the compound andan organic EL device comprising the compound are provided. In anotheraspect of the invention, an electronic device comprising the organic ELdevice is provided.

BRIEF DESCRIPTION OF DRAWINGS

FIG. 1 is a schematic view showing the structure of the organic ELdevice in an aspect of the invention.

FIG. 2 is a chart showing an emission spectrum of the compound 1synthesized in Example 1.

FIG. 3 is a chart showing an emission spectrum of the compound 2synthesized in Example 2.

FIG. 4 is a chart showing an emission spectrum of the comparativecompound 1.

FIG. 5 is a chart showing an emission spectrum of the comparativecompound 2.

FIG. 6 is a chart showing an emission spectrum of the organic EL deviceproduced in Example 3.

FIG. 7 is a chart showing an emission spectrum of the organic EL deviceproduced in Comparative Example 3.

DESCRIPTION OF EMBODIMENTS

The term of “XX to YY carbon atoms” referred to by “a substituted orunsubstituted group ZZ having XX to YY carbon atoms” used herein is thenumber of carbon atoms of the unsubstituted group ZZ and does notinclude any carbon atom in the substituent of the substituted group ZZ.“YY” is larger than “XX” and each represents an integer of 1 or more.

The term of “XX to YY atoms” referred to by “a substituted orunsubstituted group ZZ having XX to YY atoms” used herein is the numberof atoms of the unsubstituted group ZZ and does not include any atom inthe substituent of the substituted group ZZ. “YY” is larger than “XX”and each represents an integer of 1 or more.

The term of “unsubstituted group ZZ” referred to by “substituted orunsubstituted group ZZ” used herein means that no hydrogen atom in thegroup ZZ is substituted by a substituent.

The definition of “hydrogen atom” used herein includes isotopesdifferent in the neutron numbers, i.e., light hydrogen (protium), heavyhydrogen (deuterium), and tritium.

The number of “ring carbon atoms” referred to herein means the number ofthe carbon atoms included in the atoms which are members forming thering itself of a compound in which a series of atoms is bonded to form aring (for example, a monocyclic compound, a fused ring compound, across-linked compound, a carbocyclic compound, and a heterocycliccompound). If the ring has a substituent, the carbon atom in thesubstituent is not included in the ring carbon atom. The same applies tothe number of “ring carbon atom” described below, unless otherwisenoted. For example, a benzene ring has 6 ring carbon atoms, anaphthalene ring has 10 ring carbon atoms, a pyridinyl group has 5 ringcarbon atoms, and a furanyl group has 4 ring carbon atoms. If a benzenering or a naphthalene ring has, for example, an alkyl substituent, thecarbon atom in the alkyl substituent is not counted as the ring carbonatom of the benzene or naphthalene ring. In case of a fluorene ring towhich a fluorene substituent is bonded (inclusive of a spirofluorenering), the carbon atom in the fluorene substituent is not counted as thering carbon atom of the fluorene ring.

The number of “ring atom” referred to herein means the number of theatoms which are members forming the ring itself (for example, amonocyclic ring, a fused ring, and a ring assembly) of a compound inwhich a series of atoms is bonded to form the ring (for example, amonocyclic compound, a fused ring compound, a cross-linked compound, acarbocyclic compound, and a heterocyclic compound). The atom not formingthe ring (for example, hydrogen atom(s) for saturating the valence ofthe atom which forms the ring) and the atom in a substituent, if thering is substituted, are not counted as the ring atom. The same appliesto the number of “ring atoms” described below, unless otherwise noted.For example, a pyridine ring has 6 ring atoms, a quinazoline ring has 10ring atoms, and a furan ring has 5 ring atoms. The hydrogen atom on thering carbon atom of a pyridine ring or a quinazoline ring and the atomin a substituent are not counted as the ring atom. In case of a fluorenering to which a fluorene substituent is bonded (inclusive of aspirofluorene ring), the atom in the fluorene substituent is not countedas the ring atom of the fluorene ring.

The optional substituent referred to by “substituted or unsubstituted”used herein is selected from an alkyl group having 1 to 20, preferably 1to 10, and more preferably 1 to 5 carbon atoms; a mono-, di-, ortrialkylsilyl group each comprising an alkyl group having 1 to 20,preferably 1 to 10, and more preferably 1 to 5 carbon atoms; an arylgroup having 6 to 30, preferably 6 to 24, and more preferably 6 to 18ring carbon atoms; a mono-, di-, or triarylsilyl group each comprisingan aryl group having 6 to 30, preferably 6 to 24, and more preferably 6to 18 ring carbon atoms; and a heteroaryl group having 5 to 50,preferably 6 to 24, more preferably 6 to 18 ring atoms which includes 1to 5, preferably 1 to 3, more preferably 1 or 2 heteroatoms, wherein theheteroatoms are the same or different and selected from a nitrogen atom,an oxygen atom and a sulfur atom. These optional substituents may befurther substituted by the optional substituents mentioned above. Theoptional substituents may be bonded to each other to form a ring.

Examples, preferred examples, more preferred examples, and still morepreferred examples of the above optional substituents are the same asthe corresponding substituents mentioned below.

The compound in an aspect of the invention is represented by formula (1)(hereinafter also referred to as “compound (1)”).

Ar is a substituted or unsubstituted alkyl group having 1 to 20 carbonatoms, a substituted or unsubstituted aryl group having 6 to 30 ringcarbon atoms, or a substituted or unsubstituted nitrogen-comprisingheteroaryl group having 5 to 30 ring atoms.

Examples of the alkyl group having 1 to 20, preferably 1 to 10, and morepreferably 1 to 5 carbon atoms for Ar include a methyl group, an ethylgroup, a n-propyl group, an isopropyl group, a n-butyl group, anisobutyl group, a s-butyl group, a t-butyl group, a pentyl group(inclusive of isomeric groups), a hexyl group (inclusive of isomericgroups), a heptyl group (inclusive of isomeric groups), an octyl group(inclusive of isomeric groups), a nonyl group (inclusive of isomericgroups), a decyl group (inclusive of isomeric groups), an undecyl group(inclusive of isomeric groups), and a dodecyl group (inclusive ofisomeric groups), with a methyl group, an ethyl group, a n-propyl group,an isopropyl group, a n-butyl group, an isobutyl group, a s-butyl group,a t-butyl group, and a pentyl group (inclusive of isomeric groups) beingpreferred; a methyl group, an ethyl group, a n-propyl group, anisopropyl group, a n-butyl group, an isobutyl group, a s-butyl group,and a t-butyl group being more preferred, and a methyl group, an ethylgroup, an isopropyl group, and a t-butyl group being still morepreferred.

Examples of the aryl group having 6 to 30, preferably 6 to 24, and morepreferably 6 to 18 ring carbon atoms for Ar include a phenyl group, abiphenylyl group, a terphenylyl group, a naphthyl group, anacenaphthylenyl group, an anthryl group, a benzanthryl group, anaceanthryl group, a phenanthryl group, a benzo[c]phenanthryl group, aphenalenyl group, a fluorenyl group, a picenyl group, a pentaphenylgroup, a pyrenyl group, a chrysenyl group, a benzo[g]chrysenyl group, as-indanyl group, an as-indanyl group, a fluoranthenyl group, abenzo[k]fluoranthenyl group, a triphenylenyl group, abenzo[b]triphenylenyl group, and a perylenyl group, with a phenyl group,a biphenylyl group, a terphenylyl group, and a naphthyl group beingpreferred; a phenyl group, a biphenylyl group, and a terphenylyl groupbeing more preferred; and a phenyl group being still more preferred. Thearyl group mentioned above and each of the groups mentioned belowinclude position-isomeric groups (groups different in the positions offree bonds), if any.

Examples of the substituted aryl group include a phenylnaphthyl group, anaphthylphenyl group, a tolyl group, a xylyl group, a9,9-dimethylfluorenyl group, a 9,9-diphenylfluorenyl group, at-butylphenyl group, a monovalent group represented by formula (2) or(5) which is mentioned below in detail.

The nitrogen-comprising heteroaryl group having 5 to 30, preferably 6 to24, and more preferably 6 to 18 ring atoms for Ar comprises at leastone, preferably 1 to 5, more preferably 1 to 3, and still morepreferably 1 to 2 ring hetero atoms, which may be the same or differentand selected from, for example, a nitrogen atom, a sulfur atom, and anoxygen atom. The ring hetero atom comprises at least one nitrogen atom.

Examples of the nitrogen-comprising heteroaryl group include a pyrrolylgroup, a pyridyl group, a pyridazinyl group, a pyrimidinyl group, apyrazinyl group, a triazinyl group, an imidazolyl group, an oxazolylgroup, a thiazolyl group, a pyrazolyl group, an isoxazolyl group, anisothiazolyl group, an oxadiazolyl group, a thiadiazolyl group, atriazolyl group, a tetrazolyl group, an indolyl group, an isoindolylgroup, an indolizinyl group, a quinolizinyl group, a quinolyl group, anisoquinolyl group, a cinnolyl group, a phthalazinyl group, aquinazolinyl group, a quinoxalinyl group, a benzimidazolyl group, abenzoxazolyl group, a benzothiazolyl group, an indazolyl group, abenzisoxazolyl group, a benzisothiazolyl group, a carbazolyl group, aphenanthridinyl group, an acridinyl group, a phenanthrolinyl group, aphenazinyl group, a phenothiazinyl group, a phenoxazinyl group, and axanthenyl group, with a pyridyl group, a pyridazinyl group, apyrimidinyl group, a pyrazinyl group, and a triazinyl group beingpreferred, and a pyridyl group, a pyrimidinyl group, and a triazinylgroup being more preferred.

Ar is preferably a substituted or unsubstituted aryl group having 6 to30 ring carbon atoms, more preferably a phenyl group, a biphenylylgroup, a triphenylenyl group, a terphenyl group, a tolyl group, a xylylgroup, an isopropylphenyl group, a t-butylphenyl group, a naphthylgroup, or a monovalent group represented by formula (2) or (5), stillmore preferably a terphenyl group, a tolyl group, a xylyl group, anisopropylphenyl group, a t-butylphenyl group, a naphthyl group, or atriphenylenyl group, and particularly preferably a phenyl group, a tolylgroup, a xylyl group, or a t-butylphenyl group.

Each of L₁ and L₂ is independently a single bond, a substituted orunsubstituted arylene group having 6 to 30 ring carbon atoms, asubstituted or unsubstituted heteroarylene group having 5 to 30 ringatoms, or a substituted or unsubstituted divalent linking group, wherein2 to 4 groups selected from an arylene group having 6 to 30 ring carbonatoms and a heteroarylene group having 5 to 30 ring atoms are bonded toeach other via a single bond.

Examples, preferred examples, more preferred examples, and still morepreferred examples of the arylene group having 6 to 30, preferably 6 to24, and more preferably 6 to 18 ring carbon atoms for L₁ and L₂ includedivalent groups obtained by removing one hydrogen atom from the arylgroup having 6 to 30 ring carbon atoms mentioned above, preferredexample thereof, more preferred example thereof, and still morepreferred example thereof.

The heteroarylene group having 5 to 30, preferably 6 to 24, and morepreferably 6 to 18 ring atoms for L₁ and L₂ comprises at least one,preferably 1 to 5, more preferably 1 to 3, and still more preferably 1to 2 ring hetero atoms, which may be the same or different and selectedfrom, for example, a nitrogen atom, a sulfur atom, and an oxygen atom.

Examples of the heteroarylene group include divalent residues ofpyrrole, furan, thiophene, pyridine, pyridazine, pyrimidine, pyrazine,triazine, imidazole, oxazole, thiazole, pyrazole, isoxazole,isothiazole, oxadiazole, thiadiazole, triazole, tetrazole, indole,isoindole, benzofuran, isobenzofuran, benzothiophene, isobenzothiophene,indolizine, quinolizine, quinoline, isoquinoline, cinnoline,phthalazine, quinazoline, quinoxaline, benzimidazole, benzoxazole,benzothiazole, indazole, benzisoxazole, benzisothiazole, dibenzofuran,dibenzothiophene, carbazole, phenanthridine, acridine, phenanthroline,phenazine, phenothiazine, phenoxazine, and xanthene, with divalentresidues of furan, thiophene, pyridine, pyridazine, pyrimidine,pyrazine, triazine, benzofuran, benzothiophene, dibenzofuran, anddibenzothiophene being preferred, and divalent residues of benzofuran,benzothiophene, dibenzofuran, and dibenzothiophene being more preferred.

Preferably each of L₁ and L₂ is independently a single bond, asubstituted or unsubstituted arylene group having 6 to 30 ring carbonatoms, or a substituted or unsubstituted heteroarylene group having 5 to30 ring atoms, more preferably a single bond, an arylene group having 6to 30 ring carbon atoms, or a heteroarylene group having 5 to 30 ringatoms, still more preferably a single bond or an arylene group having 6to 30 ring carbon atoms, and particularly preferably a single bond.

A is a monovalent group represented by formula (2):

Each of R₁ and R₂ is independently a hydrogen atom, a substituted orunsubstituted alkyl group having 1 to 20 carbon atoms, a mono-, di-, ortrialkylsilyl group each comprising a substituted or unsubstituted alkylgroup having 1 to 20 carbon atoms, a substituted or unsubstituted arylgroup having 6 to 30 ring carbon atoms, a mono-, di-, or triarylsilylgroup each comprising a substituted or unsubstituted aryl group having 6to 30 ring carbon atoms, or a substituted or unsubstituted heteroarylgroup having 5 to 30 ring atoms, wherein R₁ and R₂ may be bonded to eachother to form a ring.

In each of R₁ and R₂, examples, preferred examples, more preferredexamples, and still more preferred examples of the alkyl group having 1to 20, preferably 1 to 10, and more preferably 1 to 5 carbon atoms; thealkyl group having 1 to 20, preferably 1 to 10, and more preferably 1 to5 carbon atoms in each of the mono-, di-, and trialkylsilyl groups; thearyl group having 6 to 30, preferably 6 to 24, and more preferably 6 to18 ring carbon atoms; and the aryl group having 6 to 30, preferably 6 to24, and more preferably 6 to 18 ring carbon atoms in each of the mono-,di-, and triarylsilyl groups are the same as the examples, the preferredexamples, the more preferred examples, and the still more preferredexamples of the alkyl group and the aryl group, which are mentionedabove with respect to Ar.

The alkylsilyl group is preferably a trimethylsilyl group, atriethylsilyl group, a t-butyldimethylsilyl group, a pyropydimethylsilylgroup, and an isopyropydimethylsilyl group, more preferably atrimethylsilyl group and a triethylsilyl group, and still morepreferably a trimethylsilyl group.

The arylsilyl group is preferably a triphenylsilyl group.

The heteroaryl group having 5 to 30, preferably 6 to 24, and morepreferably 6 to 18 ring atoms for R₁ and R₂ comprises at least one,preferably 1 to 5, more preferably 1 to 3, and still more preferably 1to 2 ring hetero atoms, which may be the same or different and selectedfrom a nitrogen atom, a sulfur atom, and an oxygen atom.

Examples of the heteroaryl group include a pyrrolyl group, a furylgroup, a thienyl group, a pyridyl group, a pyridazinyl group, apyrimidinyl group, a pyrazinyl group, a triazinyl group, an imidazolylgroup, an oxazolyl group, a thiazolyl group, a pyrazolyl group, anisoxazolyl group, an isothiazolyl group, an oxadiazolyl group, athiadiazolyl group, a triazolyl group, a tetrazolyl group, an indolylgroup, an isoindolyl group, a benzofuranyl group, an isobenzofuranylgroup, a benzothiophenyl group, an isobenzothiophenyl group, anindolizinyl group, a quinolizinyl group, a quinolyl group, anisoquinolyl group, a cinnolyl group, a phthalazinyl group, aquinazolinyl group, a quinoxalinyl group, a benzimidazolyl group, abenzoxazolyl group, a benzothiazolyl group, an indazolyl group, abenzisoxazolyl group, a benzisothiazolyl group, a dibenzofuranyl group,a dibenzothiophenyl group, a carbazolyl group, a phenanthridinyl group,an acridinyl group, a phenanthrolinyl group, a phenazinyl group, aphenothiazinyl group, a phenoxazinyl group, and a xanthenyl group, witha furyl group, a thienyl group, a pyridyl group, a pyridazinyl group, apyrimidinyl group, a pyrazinyl group, a triazinyl group, a benzofuranylgroup, a benzothiophenyl group, a dibenzofuranyl group, and adibenzothiophenyl group being preferred, and a benzofuranyl group, abenzothiophenyl group, a dibenzofuranyl group, and a dibenzothiophenylgroup being more preferred.

Preferably each of R₁ and R₂ is independently a hydrogen atom, asubstituted or unsubstituted alkyl group having 1 to 20 carbon atoms, ora substituted or unsubstituted aryl group having 6 to 30 ring carbonatoms, more preferably an alkyl group having 1 to 20 carbon atoms or anaryl group having 6 to 30 ring carbon atoms, still more preferably amethyl group, an ethyl group, a n-propyl group, an isopropyl group, or aphenyl group, and particularly preferably a methyl group.

R₁ and R₂ may be bonded to each other to form a ring. Examples of thering to be formed by R₁ and R₂ together with the carbon atom to which R₁and R₂ are bonded include a cyclopentane ring, a cyclohexane ring, afluorene ring (a 9,9-spirofluorene structure is formed together with thefluorene ring to which R₁ and R₂ are bonded).

Adjacent two groups in one pair selected from R₃ and R₄, R₄ and R₅, andR₅ and R₆ are bonded to each other to form a divalent group representedby formula (3). Adjacent two groups in one pair selected from R₇ and R₈,R₈ and R₉, and R₉ and R₁₀ are bonded to each other to form a divalentgroup represented by formula (4).

In an embodiment of the invention, formula (3) and formula (4) are thesame. In another embodiment of the invention, formula (3) is differentfrom formula (4).

Each of R₁₁ to R₁₈ is independently a hydrogen atom, a substituted orunsubstituted alkyl group having 1 to 20 carbon atoms; a mono-, di-, ortrialkylsilyl group each comprising a substituted or unsubstituted alkylgroup having 1 to 20 carbon atoms; a substituted or unsubstituted arylgroup having 6 to 30 ring carbon atoms; a mono-, di-, or triarylsilylgroup each comprising a substituted or unsubstituted aryl group having 6to 30 ring carbon atoms, or a substituted or unsubstituted heteroarylgroup having 5 to 30 ring atoms.

In R₁₁ to R₁₈, examples, preferred examples, more preferred examples,and still more preferred examples of the alkyl group having 1 to 20,preferably 1 to 10, and more preferably 1 to 5 carbon atoms; the alkylgroup having 1 to 20, preferably 1 to 10, and more preferably 1 to 5carbon atoms in each of the mono-, di-, and trialkylsilyl groups; thearyl group having 6 to 30, preferably 6 to 24, and more preferably 6 to18 ring carbon atoms; the aryl group having 6 to 30, preferably 6 to 24,and more preferably 6 to 18 ring carbon atoms in each of the mono-, di-,and triarylsilyl groups, and the heteroaryl group having 5 to 30,preferably 6 to 24, and more preferably 6 to 18 ring atoms are the sameas the examples, the preferred examples, the more preferred examples,and the still more preferred examples of the corresponding groups whichare described above with respect to R₁ and R₂.

Preferably each of R₁₁ to R₁₈ is independently a hydrogen atom, asubstituted or unsubstituted alkyl group having 1 to 20 carbon atoms, ora substituted or unsubstituted aryl group having 6 to 30 ring carbonatoms, more preferably a hydrogen atom, an alkyl group having 1 to 20carbon atoms, or an aryl group having 6 to 30 ring carbon atoms, andstill more preferably a hydrogen atom.

One selected from R₃ to R₆ which do not form the divalent grouprepresented by formula (3), R₇ to R₁₀ which do not form the divalentgroup represented by formula (4), and R₁₁ to R₁₈ is a single bond bondedto L₁.

Each of R₃ to R₁ which do not form the divalent group represented byformula (3) and is not a single bond bonded to L₁, and each of R₇ to R₁₀which do not form the divalent group represented by formula (4) and isnot a single bond bonded to L₁ is independently a hydrogen atom; asubstituted or unsubstituted alkyl group having 1 to 20 carbon atoms; amono-, di-, or trialkylsilyl group each comprising a substituted orunsubstituted alkyl group having 1 to 20 carbon atoms; a substituted orunsubstituted aryl group having 6 to 30 ring carbon atoms; a mono-, di-,or triarylsilyl group each comprising a substituted or unsubstitutedaryl group having 6 to 30 ring carbon atoms, or a substituted orunsubstituted heteroaryl group having 5 to 30 ring atoms.

Examples, preferred examples, more preferred examples, and still morepreferred examples of the alkyl group having 1 to 20, preferably 1 to10, and more preferably 1 to 5 carbon atoms; the alkyl group having 1 to20, preferably 1 to 10, and more preferably 1 to 5 carbon atoms in eachof the mono-, di-, and trialkylsilyl groups; the aryl group having 6 to30, preferably 6 to 24, and more preferably 6 to 18 ring carbon atoms;the aryl group having 6 to 30, preferably 6 to 24, and more preferably 6to 18 ring carbon atoms in each of the mono-, di-, and triarylsilylgroups; and the heteroaryl group having 5 to 30, preferably 6 to 24, andmore preferably 6 to 18 ring atoms are the same as the examples, thepreferred examples, the more preferred examples, and the still morepreferred examples of the corresponding groups which are mentioned withrespect to R₁ and R₂.

Each of R₃ to R₆ which do not form the divalent group represented byformula (3) and is not a single bond bonded to L₁, and each of R₇ to R₁₀which do not form the divalent group represented by formula (4) and isnot a single bond bonded to L₁ is independently preferably a hydrogenatom, a substituted or unsubstituted alkyl group having 1 to 20 carbonatoms, or a substituted or unsubstituted aryl group having 6 to 30 ringcarbon atoms, more preferably a hydrogen atom, an alkyl group having 1to 20 carbon atoms, or an aryl group having 6 to 30 ring carbon atoms,and still more preferably a hydrogen atom.

In formula (2), adjacent two groups selected from R₁; R₂; R₃ to R₆ notforming the divalent group represented by formula (3); R₇ to R₁₀ notforming the divalent group represented by formula (4); R₁₁ to R₁₄; andR₁₅ to R₁₈ are not bonded to each other thereby failing to form a ring,provided that a pair of R₁ and R₂ may be bonded to each other to form aring.

Namely, only one monocyclic ring is fused to each of two benzene ringsof the fluorene structure of formula (2), i.e., two or more rings do notfuse to each benzene ring of the fluorene structure of formula (2), andalso, a ring comprising two or more rings does not fuse thereto.

Formula (2) (inclusive of formula (2) for Ar) is preferably representedby any of formulae (6) to (11), more preferably represented by any offormulae (6), (8), and (9), and still more preferably represented byformula (6) or (9).

In formulae (6) to (11), R₁ to R₁₈ are as defined above.

In formula (6), one of R₅ to R₈ and R₁₁ to R₁₈, preferably R₁₃ or R₁₆ isa single bond which is bonded to L₁.

In formula (7), one of R₅, R₆, R₉, R₁₀, and R₁₁ to R₁₈, preferably R₅,R₉, or R₁₃ is a single bond which is bonded to L₁.

In formula (8), one of R₃, R₄, R₉, R₁₀, and R₁₁ to R₁₈, preferably R₄ orR₉ is a single bond which is bonded to L₁.

In formula (9), one of R₃, R₆, R₇, R₁₀, and R₁₁ to R₁₈, preferably R₁₂or R₁₇ is a single bond which is bonded to L₁.

In formula (10), one of R₅ to R₇, R₁₀, and R₁₁ to R₁₈, preferably R₇,R₁₃, or R₁₇ is a single bond which is bonded to L₁.

In formula (11), one of R₃, R₄, R₇, R₁₀, and R₁₁ to R₁₈, preferably R₄or R₁₇ is a single bond which is bonded to L₁.

B is a monovalent group represented by formula (5):

Each of R₂₁ and R₂₂ is independently a hydrogen atom, a substituted orunsubstituted alkyl group having 1 to 20 carbon atoms, a mono-, di-, ortrialkylsilyl group each comprising a substituted or unsubstituted alkylgroup having 1 to 20 carbon atoms, a substituted or unsubstituted arylgroup having 6 to 30 ring carbon atoms, a mono-, di-, or triarylsilylgroup each comprising a substituted or unsubstituted aryl group having 6to 30 ring carbon atoms, or a substituted or unsubstituted heteroarylgroup having 5 to 30 ring atoms, wherein R₂₁ and R₂₂ may be bonded toeach other to form a ring.

In R₂₁ and R₂₂, examples, preferred examples, more preferred examples,and still more preferred examples of the alkyl group having 1 to 20,preferably 1 to 10, and more preferably 1 to 5 carbon atoms; the alkylgroup having 1 to 20, preferably 1 to 10, and more preferably 1 to 5carbon atoms in each of the mono-, di-, and trialkylsilyl groups; thearyl group having 6 to 30, preferably 6 to 24, and more preferably 6 to18 ring carbon atoms; the aryl group having 6 to 30, preferably 6 to 24,and more preferably 6 to 18 ring carbon atoms in each of the mono-, di-,and triarylsilyl groups, and the heteroaryl group having 5 to 30,preferably 6 to 24, and more preferably 6 to 18 ring atoms are the sameas the examples, the preferred examples, the more preferred examples,and the still more preferred examples of the corresponding groups whichare described above with respect to R₁ and R₂.

Preferably each of R₂₁ and R₂₂ is independently a hydrogen atom, asubstituted or unsubstituted alkyl group having 1 to 20 carbon atoms, ora substituted or unsubstituted aryl group having 6 to 30 ring carbonatoms, more preferably an alkyl group having 1 to 20 carbon atoms or anaryl group having 6 to 30 ring carbon atoms, still more preferably amethyl group, an ethyl group, a n-propyl group, an isopropyl group, or aphenyl group, and particularly preferably a methyl group.

R₂₁ and R₂₂ may be bonded to each other to form a ring. Examples of thering to be formed by R₂₁ and R₂₂ together with the carbon atom to whichR₂₁ and R₂₂ are bonded include a cyclopentane ring, a cyclohexane ring,a fluorene ring (a 9,9-spirofluorene structure is formed together withthe fluorene ring to which R₂₁ and R₂₂ are bonded).

Each of R₂₃ to R₃₀ is independently a hydrogen atom, a substituted orunsubstituted alkyl group having 1 to 20 carbon atoms; a mono-, di-, ortrialkylsilyl group each comprising a substituted or unsubstituted alkylgroup having 1 to 20 carbon atoms; a substituted or unsubstituted arylgroup having 6 to 30 ring carbon atoms; a mono-, di-, or triarylsilylgroup each comprising a substituted or unsubstituted aryl group having 6to 30 ring carbon atoms; or a substituted or unsubstituted heteroarylgroup having 5 to 30 ring atoms. One selected from R₂₇ to R₃₀ may be asingle bond bonded to L₂.

In R₂₃ to R₃₀, examples, preferred examples, more preferred examples,and still more preferred examples of the alkyl group having 1 to 20,preferably 1 to 10, and more preferably 1 to 5 carbon atoms; the alkylgroup having 1 to 20, preferably 1 to 10, and more preferably 1 to 5carbon atoms in each of the mono-, di-, and trialkylsilyl groups; thearyl group having 6 to 30, preferably 6 to 24, and more preferably 6 to18 ring carbon atoms; the aryl group having 6 to 30, preferably 6 to 24,and more preferably 6 to 18 ring carbon atoms in each of the mono-, di-,and triarylsilyl groups, and the heteroaryl group having 5 to 30,preferably 6 to 24, and more preferably 6 to 18 ring atoms are the sameas the examples, the preferred examples, the more preferred examples,and the still more preferred examples of the corresponding groups whichare described above with respect to R₁ and R₂.

Preferably each of R₂₃ to R₃₀ is independently a hydrogen atom, asubstituted or unsubstituted alkyl group having 1 to 20 carbon atoms, ora substituted or unsubstituted aryl group having 6 to 30 ring carbonatoms, more preferably a hydrogen atom, an alkyl group having 1 to 20carbon atoms, or an aryl group having 6 to 30 ring carbon atoms, andstill more preferably a hydrogen atom.

Adjacent groups in one or two pairs selected from R₂₃ and R₂₄, R₂₄ andR₂₅, and R₂₅ and R₂₆ may be bonded to each other to form a ring.

Adjacent groups in one or two pairs selected from R₂₇ and R₂₈, R₂₈ andR₂₉, and R₂₉ and R₃₀ may be bonded to each other to form a carbon ring.

In formula (5), one selected from R₂₇ to R₃₀ which do not form theoptional carbon ring is a single bond bonded to L₂, or one of ringcarbon atoms of the carbon ring which is optionally formed by one pairselected from R₂₇ and R₂₈, R₂₈ and R₂₉, and R₂₉ and R₃₀ is bonded to L₂.

The divalent group which is optionally formed by one or two pairsselected from R₂₃ and R₂₄, R₂₄ and R₂₅, and R₂₅ and R₂₆ is preferablyrepresented by formula (12) or (13). The divalent group which isoptionally formed by one or two pairs selected from R₂₇ and R₂₈, R₂₈ andR₂₉, and R₂₉ and R₃₀ is preferably represented by formula (14).

Each of R₃₁ to R₃₄, R₃₅ to R₃₈, and R₃₉ to R₄₂ is independently ahydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20carbon atoms, a mono-, di-, or trialkylsilyl group each comprising asubstituted or unsubstituted alkyl group having 1 to 20 carbon atoms, asubstituted or unsubstituted aryl group having 6 to 30 ring carbonatoms, a mono-, di-, or triarylsilyl group each comprising a substitutedor unsubstituted aryl group having 6 to 30 ring carbon atoms, or asubstituted or unsubstituted heteroaryl group having 5 to 30 ring atoms.

Adjacent two groups respectively selected from R₃₁ to R₃₄, R₃₅ to R₃₈,and R₃₉ to R₄₂ may be bonded to each other to form, together with thecarbon atoms to which two groups are bonded, a ring, such as a benzenering.

In R₃₁ to R₃₄, R₃₅ to R₃₈, and R₃₉ to R₄₂, examples, preferred examples,more preferred examples, and still more preferred examples of the alkylgroup having 1 to 20, preferably 1 to 10, and more preferably 1 to 5carbon atoms; the alkyl group having 1 to 20, preferably 1 to 10, andmore preferably 1 to 5 carbon atoms in each of the mono-, di-, andtrialkylsilyl groups; the aryl group having 6 to 30, preferably 6 to 24,and more preferably 6 to 18 ring carbon atoms; the aryl group having 6to 30, preferably 6 to 24, and more preferably 6 to 18 ring carbon atomsin each of the mono-, di-, and triarylsilyl groups, and the heteroarylgroup having 5 to 30, preferably 6 to 24, and more preferably 6 to 18ring atoms are the same as the examples, the preferred examples, themore preferred examples, and the still more preferred examples of thecorresponding groups which are described above with respect to R₁ andR₂.

One of R₃₉ to R₄₂ may be a single bond which is bonded to L₂.

Preferably each of R₃₁ to R₃₄, R₃₅ to R₃₈, and R₃₉ to R₄₂ isindependently a hydrogen atom, a substituted or unsubstituted alkylgroup having 1 to 20 carbon atoms, or a substituted or unsubstitutedaryl group having 6 to 30 ring carbon atoms, more preferably a hydrogenatom, an alkyl group having 1 to 20 carbon atoms, or an aryl grouphaving 6 to 30 ring carbon atoms, and still more preferably a hydrogenatom.

X is CR₄₃R₄₄, NR₄₅, O, or S.

Each of R₄₃ to R₄₅ is independently a hydrogen atom, a substituted orunsubstituted alkyl group having 1 to 20 carbon atoms; a mono-, di-, ortrialkylsilyl group each comprising a substituted or unsubstituted alkylgroup having 1 to 20 carbon atoms; a substituted or unsubstituted arylgroup having 6 to 30 ring carbon atoms; a mono-, di-, or triarylsilylgroup each comprising a substituted or unsubstituted aryl group having 6to 30 ring carbon atoms; or a substituted or unsubstituted heteroarylgroup having 5 to 30 ring atoms, wherein R₄₃ and R₄₄ may be bonded toeach other to form a ring.

In R₄₃ to R₄₅, examples, preferred examples, more preferred examples,and still more preferred examples of the alkyl group having 1 to 20,preferably 1 to 10, and more preferably 1 to 5 carbon atoms; the alkylgroup having 1 to 20, preferably 1 to 10, and more preferably 1 to 5carbon atoms in each of the mono-, di-, and trialkylsilyl groups; thearyl group having 6 to 30, preferably 6 to 24, and more preferably 6 to18 ring carbon atoms; the aryl group having 6 to 30, preferably 6 to 24,and more preferably 6 to 18 ring carbon atoms in each of the mono-, di-,and triarylsilyl groups, and the heteroaryl group having 5 to 30,preferably 6 to 24, and more preferably 6 to 18 ring atoms are the sameas the examples, the preferred examples, the more preferred examples,and the still more preferred examples of the corresponding groups whichare described above with respect to R₁ and R₂.

Each of R₄₃ and R₄₄ is preferably a hydrogen atom, a substituted orunsubstituted alkyl group having 1 to 20 carbon atoms, or a substitutedor unsubstituted aryl group having 6 to 30 ring carbon atoms, morepreferably a hydrogen atom, an alkyl group having 1 to 20 carbon atoms,or an aryl group having 6 to 30 ring carbon atoms, and still morepreferably a methyl group or a phenyl group.

R₄₅ is preferably a hydrogen atom, a substituted or unsubstituted alkylgroup having 1 to 20 carbon atoms, or a substituted or unsubstitutedaryl group having 6 to 30 ring carbon atoms, more preferably a hydrogenatom, an alkyl group having 1 to 20 carbon atoms, or an aryl grouphaving 6 to 30 ring carbon atoms, and still more preferably a phenylgroup.

Formula (5) is preferably represented by any of formulae (15) to (54),more preferably any of formula (15), (18), (19), (24), (25), (26), (28)to (37), and (39) to (41), and still more preferably any of formulae(15), (19), (28), (30) to (33), (35), (36), and (37).

In formulae (15) to (54), R₂₁ to R₄₅ are as defined above.

In formula (15), one of R₂₇, R₂₈, and R₃₉ to R₄₂, preferably R₄₀ is asingle bond which is bonded to L₂.

In formula (16), one of R₂₉, R₃₀, and R₃₉ to R₄₂, preferably R₂₉ is asingle bond which is bonded to L₂.

In formula (17), one of R₂₇, R₂₈, and R₃₉ to R₄₂, preferably R₂₈ or R₄₀is a single bond which is bonded to L₂.

In formula (18), one of R₂₉, R₃₀, and R₃₉ to R₄₂, preferably R₂₉ is asingle bond which is bonded to L₂.

In formula (19), one of R₂₇, R₃₀, and R₃₉ to R₄₂, preferably R₄₁ is asingle bond which is bonded to L₂.

In formula (20), one of R₂₇, R₃₀, and R₃₉ to R₄₂, preferably R₂₇ or R₄₁is a single bond which is bonded to L₂.

In formula (21), one of R₂₇, R₂₈, and R₃₉ to R₄₂, preferably R₄₀ is asingle bond which is bonded to L₂.

In formula (22), one of R₂₇, R₃₀, and R₃₉ to R₄₂, preferably R₄₁ is asingle bond which is bonded to L₂.

In formula (23), one of R₂₉, R₃₀, and R₃₉ to R₄₂, preferably R₂₉ is asingle bond which is bonded to L₂.

In formula (24), two groups R₃₁, two groups R₃₂, two groups R₃₃, and twogroups R₃₄ may be the same or different, respectively, and one of R₂₇ toR₃₀, preferably R₂₉ is a single bond which is bonded to L₂.

In formula (25), two groups R₃₉, two groups R₄₀, two groups R₄₁, and twogroups R₄₂ may be the same or different, respectively, and one of thesegroups, preferably R₄₀ on the benzene ring fused to the position 1-2(side a) of the fluorene structure is a single bond which is bonded toL₂.

In formula (26), one of R₂₇ to R₃₀, preferably R₂₉ is a single bondwhich is bonded to L₂.

In formula (27), one of R₂₇ to R₃₀, preferably R₂₇ or R₂₉ is a singlebond which is bonded to L₂.

In formula (28), one of R₂₇ to R₃₀, preferably R₂₉ is a single bondwhich is bonded to L₂.

In formula (29), one of R₂₉, R₃₀, and R₃₉ to R₄₂, preferably R₂₉ is asingle bond which is bonded to L₂.

In formula (30), one of R₂₇ to R₃₀, preferably one of R₂₇ to R₂₉ is asingle bond which is bonded to L₂.

In formulae (31) to (54), one of R₂₇ to R₃₀, preferably R₂₉ is a singlebond which is bonded to L₂.

In an embodiment of the invention, the compound (1) is represented byformula (1) wherein Ar is a monovalent group represented by formula (5),and B and Ar are preferably the same.

In another embodiment of the invention, the compound (1) is representedby formula (1) wherein A and B are the same, preferably A beingrepresented by any of formulae (6) to (11), and B being represented byany of formulae (15) to (23).

In still another embodiment of the invention, the compound (1) isrepresented by formula (1) wherein Ar is a monovalent group representedby formula (2), preferably, each of A and Ar is represented by any offormulae (6) to (11), B is represented by any of formulae (15) to (23),and A, B, and Ar are the same.

The compound (1) is useful as a material for organic EL device,particularly as a dopant material for a fluorescent emitting layer. Theproduction method of the compound (1) is not limited, and one ofordinary skill in the art can easily produce the compound (1) by usingor modifying the known synthesis reaction with reference to the examplesdescribed below.

Examples of the compound (1) are shown below, although not limitedthereto.

Organic Electroluminescence Device

The organic EL device in an aspect of the invention will be describedbelow.

The organic EL device comprises at least one of organic thin film layerbetween a cathode and an anode. The at least one of organic thin filmlayer comprise a light emitting layer, and at least one layer of the atleast one of organic thin film layer comprises the compound representedby formula (1) (compound (1)).

Examples of the organic thin film layer which comprises the compound (1)include an anode-side organic thin film layer formed between an anodeand a light emitting layer (hole transporting layer, hole injectinglayer, etc.), a light emitting layer, a cathode-side organic thin filmlayer formed between a cathode and a light emitting layer (electrontransporting layer, electron injecting layer, etc.), a space layer, anda blocking layer, although not limited thereto. The compound (1) isusable as, for example, a host material or a dopant material for use ina light emitting layer of a fluorescent emission unit, a host materialfor use in a light emitting layer of a phosphorescent emission unit, anda hole transporting layer material or an electron transporting layermaterial in an emission unit, and preferably usable as a host materialor a dopant material for use in a light emitting layer of a fluorescentemission unit, a host material for use in a light emitting layer of aphosphorescent emission unit, and a hole transporting layer material inan emission unit.

The organic EL device in an aspect of the invention may be any of afluorescent or phosphorescent single color emitting device, awhite-emitting device of fluorescent-phosphorescent hybrid type, asimple-type emitting device having a single emission unit, and a tandememitting device having two or more emission units, with a fluorescentdevice being preferred. The “emission unit” referred to herein is thesmallest unit for emitting light by the recombination of injected holesand injected electrons, which comprises one or more organic thin filmlayers wherein at least one layer is a light emitting layer.

Representative device structures of the simple-type organic EL deviceare shown below:

(1) Anode/Emission Unit/Cathode

The emission unit may be a laminated unit comprising two or more layersselected from a phosphorescent light emitting layer and a fluorescentlight emitting layer. A space layer may be disposed between the lightemitting layers to prevent the diffusion of excitons generated in thephosphorescent light emitting layer into the fluorescent light emittinglayer. Representative layered structures of the simple-type emissionunit are shown below:

(a) hole transporting layer/fluorescent emitting layer (/electrontransporting layer);

(b) hole transporting layer/first fluorescent emitting layer/secondfluorescent emitting layer (/electron transporting layer);

(c) hole transporting layer/phosphorescent emitting layer/spacelayer/fluorescent emitting layer (/electron transporting layer);

(d) hole transporting layer/first phosphorescent emitting layer/secondphosphorescent emitting layer/space layer/fluorescent emitting layer(/electron transporting layer);

(e) hole transporting layer/first phosphorescent emitting layer/spacelayer/second phosphorescent emitting layer/space layer/fluorescentemitting layer (/electron transporting layer);

(f) hole transporting layer/phosphorescent emitting layer/spacelayer/first fluorescent emitting layer/second fluorescent emitting layer(/electron transporting layer);

(g) hole transporting layer/electron blocking layer/fluorescent emittinglayer (/electron transporting layer);

(h) hole transporting layer/fluorescent emitting layer/hole blockinglayer (/electron transporting layer); and

(i) hole transporting layer/fluorescent emitting layer/triplet blockinglayer (/electron transporting layer).

The emission color of the fluorescent emitting layer and that of thephosphorescent emitting layer may be different. For example, the layeredstructure of the laminated emission unit (d) may be hole transportinglayer/first phosphorescent emitting layer (red emission)/secondphosphorescent emitting layer (green emission)/space layer/fluorescentemitting layer (blue emission)/electron transporting layer.

An electron blocking layer may be disposed between the light emittinglayer and the hole transporting layer or between the light emittinglayer and the space layer, if necessary. Also, a hole blocking layer maybe disposed between the light emitting layer and the electrontransporting layer, if necessary. With such an electron blocking layeror a hole blocking layer, electrons and holes are confined in the lightemitting layer to increase the charge recombination in the lightemitting layer, thereby improving the emission efficiency.

Representative device structure of the tandem-type organic EL device isshown below:

(2) Anode/First Emission Unit/Intermediate Layer/Second EmissionUnit/Cathode.

The layered structure of the first emission unit and the second emissionunit may be selected from those described above with respect to theemission unit.

Generally, the intermediate layer is also called an intermediateelectrode, an intermediate conductive layer, a charge generation layer,an electron withdrawing layer, a connecting layer, or an intermediateinsulating layer. The intermediate layer may be formed by knownmaterials which can supply electrons to the first emission unit andholes to the second emission unit.

A schematic structure of an example of the organic EL device is shown inFIG. 1, wherein the organic EL device 1 comprises a substrate 2, ananode 3, a cathode 4, and an emission unit 10 disposed between the anode3 and the cathode 4. The emission unit 10 comprises a light emittinglayer 5. A hole injecting/transporting layer 6 (anode-side organic thinfilm layer) may be disposed between the light emitting layer 5 and theanode 3, and an electron injecting/transporting layer 7 (cathode-sideorganic thin film layer) may be disposed between the light emittinglayer 5 and the cathode 4. An electron blocking layer (not shown) may bedisposed on the side of anode 3 of the light emitting layer 5, and ahole blocking layer (not shown) may be disposed on the side of cathode 4of the light emitting layer 5. With these blocking layers, electrons andholes are confined in the light emitting layer 5 to increase the excitongeneration in the light emitting layer 5.

In the present specification, a host is referred to as a fluorescenthost when combinedly used with a fluorescent dopant (fluorescentemitting material) and as a phosphorescent host when combinedly usedwith a phosphorescent dopant. Therefore, the fluorescent host and thephosphorescent host are not distinguished from each other merely by thedifference in their molecular structures. Namely, in the presentinvention, the term “phosphorescent host” means a material forconstituting a phosphorescent emitting layer containing a phosphorescentdopant and does not mean a material that cannot be utilized as amaterial for a fluorescent emitting layer. The same applies to thefluorescent host.

Substrate

The substrate is a support for the emitting device and made of, forexample, glass, quartz, and plastics. The substrate may be a flexiblesubstrate, for example, a plastic substrate made of polycarbonate,polyarylate, polyether sulfone, polypropylene, polyester, polyvinylfluoride, and polyvinyl chloride. An inorganic deposition film is alsousable.

Anode

The anode is formed on the substrate preferably from a metal, an alloy,an electrically conductive compound, and a mixture thereof, each havinga large work function, for example, 4.5 eV or more. Examples of thematerial for the anode include indium oxide-tin oxide (ITO: indium tinoxide), indium oxide-tin oxide doped with silicon or silicon oxide,indium oxide-zinc oxide, indium oxide doped with tungsten oxide and zincoxide, and graphene. In addition, gold (Au), platinum (Pt), nickel (Ni),tungsten (W), chromium (Cr), molybdenum (Mo), iron (Fe), cobalt (Co),copper (Cu), palladium (Pd), titanium (Ti), and a nitride of the abovemetal (for example, titanium nitride) are also usable.

These materials are made into a film generally by a sputtering method.For example, a film of indium oxide-zinc oxide is formed by sputteringan indium oxide target doped with 1 to 10 wt % of zinc oxide, and a filmof indium oxide doped with tungsten oxide and zinc oxide is formed bysputtering an indium oxide target doped with 0.5 to 5 wt % of tungstenoxide and 0.1 to 1 wt % of zinc oxide. In addition, a vacuum vapordeposition method, a coating method, an inkjet method, and a spincoating method are usable.

A hole injecting layer to be optionally formed in contact with the anodeis formed from a composite material which is capable of easily injectingholes independently of the work function of the anode. Therefore, when ahole injecting layer is provided, the anode can be formed by a variouskind of material which is usable as an electrode material, for example,a metal, an alloy, an electroconductive compound, a mixture thereof, anda group 1 element and a group 2 element of the periodic table.

A material having a small work function, for example, the group 1element and the group 2 element of the periodic table, i.e., an alkalimetal, such as lithium (Li) and cesium (Cs), an alkaline earth metal,such as magnesium (Mg), calcium (Ca), and strontium (Sr), and an alloythereof, such as MgAg and AlLi, are also usable. In addition, a rareearth metal, such as europium (Eu) and ytterbium (Yb), and an alloythereof are also usable. The alkali metal, the alkaline earth metal, andthe alloy thereof can be made into the anode by a vacuum vapordeposition or a sputtering method. When a silver paste, etc. is used, acoating method and an inkjet method are usable.

Hole Injecting Layer

The hole injecting layer comprises a highly hole injecting material.Examples of the highly hole injecting material include molybdenum oxide,titanium oxide, vanadium oxide, rhenium oxide, ruthenium oxide, chromiumoxide, zirconium oxide, hafnium oxide, tantalum oxide, silver oxide,tungsten oxide, and manganese oxide.

The following low molecular aromatic amine compound is also usable:4,4′,4″-tris(N,N-diphenylamino)triphenylamine (TDATA),4,4′,4″-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine (MTDATA),4,4′-bis[N-(4-diphenylaminophenyl)-N-phenylamino]biphenyl (DPAB),4,4′-bis(N-({4-[N′-(3-methylphenyl)-N′-phenylamino]phenyl}-N-phenylamino)biphenyl(DNTPD), 1,3,5-tris[N-(4-diphenylaminophenyl)-N-phenylamino]benzene(DPA3B), 3-[N-(9-phenylcarbazole-3-yl)-N-phenylamino]-9-phenylcarbazole(PCzPCA1),3,6-bis[N-(9-phenylcarbazole-3-yl)-N-phenylamino]-9-phenylcarbazole(PCzPCA2), and3-[N-(1-naphthyl)-N-(9-phenylcarbazole-3-yl)amino]-9-phenylcarbazole(PCzPCN1).

A macromolecular compound, such as an oligomer, a dendrimer, a polymer,is also usable. Examples thereof include poly(N-vinylcarbazole) (PVK),poly(4-vinyltriphenylamine) (PVTPA),poly[N-(4-{N′-[4-(4-diphenylamino)phenyl]phenyl-N′-phenylamino}phenyl)methacrylamide](PTPDMA), and poly[N,N′-bis(4-butylphenyl)-N,N′-bis(phenyl)benzidine](Poly-TPD). An acid-added macromolecular compound, such aspoly(3,4-ethylenedioxythiophene)/poly(styrenesulfonic acid) (PEDOT/PSS)and polyaniline/poly(styrenesulfonic acid) (PAni/PSS), is also usable.

Hole Transporting Layer

The hole transporting layer comprises a highly hole-transportingmaterial. The hole transporting layer may contain an aromatic aminecompound, a carbazole derivative, an anthracene derivative, etc., forexamples, an aromatic amine compound, such as4,4′-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (NPB),N,N′-bis(3-methylphenyl)-N,N′-diphenyl-[1,1′-biphenyl]-4,4′-diamine(TPD), 4-phenyl-4′-(9-phenylfluorene-9-yl)triphenylamine (BAFLP),4,4′-bis[N-(9,9-dimethylfluorene-2-yl)-N-phenylamino]biphenyl (DFLDPBi),4,4′,4″-tris(N,N-diphenylamino)triphenylamine (TDATA),4,4′,4″-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine (MTDATA),and 4,4′-bis[N-(spiro-9,9′-bifluorene-2-yl)-N-phenylamino]biphenyl(BSPB). The above compounds have a hole mobility of mainly 10⁻⁶ cm²/Vsor more.

The hole transporting layer may comprise a carbazole derivative, such as4,4′-di(9-carbazolyl)biphenyl (CBP),9-[4-(9-carbazolyl)phenyl]-10-phenylanthracene (CzPA), and9-phenyl-3-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole (PCzPA); ananthracene derivative, such as 2-t-butyl-9,10-di(2-naphthyl)anthracene(t-BuDNA), 9,10-di(2-naphthyl)anthracene (DNA), and9,10-diphenylanthracene (DPAnth); and a macromolecular compound, such aspoly(N-vinylcarbazole) (PVK) and poly(4-vinyltriphenylamine) (PVTPA).

Other materials are also usable if their hole transporting ability ishigher than their electron transporting ability. The layer comprising ahighly hole-transporting material may be a single layer or a laminate oftwo or more layers each comprising the material mentioned above.

Dopant Material of Light Emitting Layer

The light emitting layer comprises a highly light-emitting material andmay be formed from a various kind of materials. For example, afluorescent emitting compound and a phosphorescent emitting compound areusable as the highly light-emitting material. The fluorescent emittingcompound is a compound capable of emitting light from a singlet excitedstate, and the phosphorescent emitting compound is a compound capable ofemitting light from a triplet excited state.

In an embodiment of the invention, at least one light emitting layer ofthe organic EL device preferably comprises the compound (1), morepreferably as a fluorescent dopant material. The following lightemitting materials (dopant materials) other than the compound (1) arealso usable in the light emitting layer.

Examples of blue fluorescent emitting material for use in the lightemitting layer include a pyrene derivative, a styrylamine derivative, achrysene derivative, a fluoranthene derivative, a fluorene derivative, adiamine derivative, and a triarylamine derivative, such asN,N′-bis[4-(9H-carbazole-9-yl)phenyl]-N,N′-diphenylstilbene-4,4′-diamine(YGA2S), 4-(9H-carbazole-9-yl)-4′-(10-phenyl-9-anthryl)triphenylamine(YGAPA), and 4-(10-phenyl-9-anthryl)-4′-(9-phenyl-9H-carbazole-3-yl)triphenylamine (PCBAPA).

Examples of green fluorescent emitting material for use in the lightemitting layer include an aromatic amine derivative, such asN-(9,10-diphenyl-2-anthryl)-N,9-diphenyl-9H-carbazole-3-amine (2PCAPA),N-[9,10-bis(1,1′-biphenyl-2-yl)-2-anthryl]-N,9-diphenyl-9H-carbazole-3-amine(2PCABPhA),N-(9,10-diphenyl-2-anthryl)-N,N′,N′-triphenyl-1,4-phenylenediamine(2DPAPA),N-[9,10-bis(1,1′-biphenyl-2-yl)-2-anthryl]-N,N′,N′-triphenyl-1,4-phenylenediamine(2DPABPhA),N-[9,10-bis(1,1′-biphenyl-2-yl)]-N-[4-(9H-carbazole-9-yl)phenyl]-N-phenylanthracene-2-amine(2YGABPhA), and N,N,9-triphenylanthracene-9-amine (DPhAPhA).

Examples of red fluorescent emitting material for use in the lightemitting layer include a tetracene derivative and a diamine derivative,such as N,N,N′,N′-tetrakis(4-methylphenyl)tetracene-5,11-diamine(p-mPhTD) and7,14-diphenyl-N,N,N′,N′-tetrakis(4-methylphenyl)acenaphtho[1,2-a]fluoranthene-3,10-diamine(p-mPhAFD).

Examples of blue phosphorescent emitting material for use in the lightemitting layer include a metal complex, such as an iridium complex, anosmium complex, and a platinum complex. Examples thereof includebis[2-(4′,6′-difluorophenyl)pyridinato-N,C2′]iridium(III)tetrakis(1-pyrazolyl)borato (FIr₆),bis[2-(4′,6′-difluorophenyl)pyridinato-N,C2′]iridium(III) picolinato(FIrpic),bis[2-(3′,5′-bistrifluoromethylphenyl)pyridinato-N,C2′]iridium(III)picolinato (Ir(CF₃ppy)₂(pic)), andbis[2-(4′,6′-difluorophenyl)pyridinato-N,C2′]iridium(III)acetylacetonato (FIracac).

Examples of green phosphorescent emitting material for use in the lightemitting layer include an iridium complex, such astris(2-phenylpyridinato-N,C2′(Ir(ppy)₃),bis(2-phenylpyridinato-N,C2′)iridium(III) acetylacetonato(Ir(ppy)₂(acac)), bis(1,2-diphenyl-1H-benzimidazolato)iridium(III)acetylacetonato (Ir(pbi)₂(acac)), andbis(benzo[h]quinolinato)iridium(III) acetylacetonato (Ir(bzq)₂(acac)).

Examples of red phosphorescent emitting material for use in the lightemitting layer include a metal complex, such as an iridium complex, aplatinum complex, a terbium complex, and a europium complex. Examplesthereof include an organometallic complex, such asbis[2-(2′-benzo[4,5-α]thienyl)pyridinato-N,C3′]iridium(III)acetylacetonato (Ir(btp)₂(acac)),bis(1-phenylisoquinolinato-N,C2′)iridium(III) acetylacetonato(Ir(piq)₂(acac)),(acetylacetonato)bis[2,3-bis(4-fluorophenyl)quinoxalinato]iridium(III)(Ir(Fdpq)₂(acac)), and 2,3,7,8,12,13,17,18-octaethyl-21H,23H-porphyrinplatinum(II) (PtOEP).

A rare earth metal complex, such as tris(acetylacetonato)(monophenanthroline)terbium(III) (Tb(acac)₃(Phen)),tris(1,3-diphenyl-1,3-propanedionato)(monophenanthroline)europium(III)(Eu(DBM)₃(Phen)), andtris[1-(2-thenoyl)-3,3,3-trifluoroacetonato](monophenanthroline)europium(III)(Eu(TTA)₃(Phen)), emits light from the rare earth metal ion (electrontransition between different multiple states), and therefore, usable asa phosphorescent emitting compound.

Host Material for Light Emitting Layer

The light emitting layer may be formed by dispersing the highlylight-emitting material (dopant material) mentioned above in anothermaterial (host material). The host material may be selected from variouskinds of materials and is preferably a material having a lowestunoccupied molecular orbital level (LUMO level) higher than that of thedopant material and a highest occupied molecular orbital level (HOMOlevel) lower than that of the dopant material.

The host material may include, for example, (1) a metal complex, such asan aluminum complex, a beryllium complex, and a zinc complex; (2) aheterocyclic compound, such as an oxadiazole derivative, a benzimidazolederivative, and a phenanthroline derivative; (3) a fused aromaticcompound, such as a carbazole derivative, an anthracene derivative, aphenanthrene derivative, a pyrene derivative, and a chrysene derivative;and (4) an aromatic amine compound, such as a triarylamine derivativeand a fused aromatic polycyclic amine derivative.

Examples thereof include a metal complex, such astris(8-quinolinolato)aluminum(III) (Alq),tris(4-methyl-8-quinolinolato)aluminum(III) (Almq₃),bis(10-hydroxybenzo[h]quinolinato)beryllium(II) (BeBq₂),bis(2-methyl-8-quinolinolato)(4-phenylphenolato)aluminum(III) (BAlq),bis(8-quinolinolato)zinc(II) (Znq),bis[2-(2-benzoxazolyl)phenolato]zinc(II) (ZnPBO), andbis[2-(2-benzothiazolyl)phenolato]zinc(II) (ZnBTZ); a heterocycliccompound, such as2-(4-biphenylyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (PBD),1,3-bis[5-(p-tert-butylphenyl)-1,3,4-oxadiazole-2-yl]benzene (OXD-7),3-(4-biphenylyl)-4-phenyl-5-(4-tert-butylphenyl)-1,2,4-triazole (TAZ),2,2′,2″-(1,3,5-benzenetriyl)tris(1-phenyl-1H-benzimidazole) (TPBI),bathophenanthroline (BPhen), and bathocuproin (BCP); a fused aromaticcompound, such as 9-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole (CzPA),3,6-diphenyl-9-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole (DPCzPA),9,10-bis(3,5-diphenylphenyl)anthracene (DPPA),9,10-di(2-naphthyl)anthracene (DNA),2-tert-butyl-9,10-di(2-naphthyl)anthracene (t-BuDNA), 9,9′-bianthryl(BANT), 9,9′-(stilbene-3,3′-diyl)diphenanthrene (DPNS),9,9′-(stilbene-4,4′-diyl)diphenanthrene (DPNS2),3,3′,3″-(benzene-1,3,5-triyl)tripyrene (TPB3), 9,10-diphenylanthracene(DPAnth), and 6,12-dimethoxy-5,11-diphenylchrysene; and an aromaticamine compound, such asN,N-diphenyl-9-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole-3-amine(CzA1PA), 4-(10-phenyl-9-anthryl)triphenylamine (DPhPA),N,9-diphenyl-N-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole-3-amine(PCAPA),N,9-diphenyl-N-{4-[4-(10-phenyl-9-anthryl)phenyl]phenyl}-9H-carbazole-3-amine(PCAPBA), N-(9,10-diphenyl-2-anthryl)-N,9-diphenyl-9H-carbazole-3-amine(2PCAPA), 4,4′-bis[N-(1-anthryl)-N-phenylamino]biphenyl (NPB or α-NPD),N,N′-bis(3-methylphenyl)-N,N′-diphenyl-[1,1′-biphenyl]-4,4′-diamine(TPD), 4,4′-bis[N-(9,9-dim-ethylfluorene-2-yl)-N-phenylamino]biphenyl(DFLDPBi), and4,4′-bis[N-(spiro-9,9′-bifluorene-2-yl)-N-phenylamino]biphenyl (BSPB).The host material may be used alone or in combination of tow or more.

Electron Transporting Layer

The electron transporting layer comprises a highly electron-transportingmaterial, for example, (1) a metal complex, such as an aluminum complex,a beryllium complex, and a zinc complex; (2) a heteroaromatic compound,such as an imidazole derivative, a benzimidazole derivative, an azinederivative, a carbazole derivative, and a phenanthroline derivative; and(3) a macromolecular compound. Examples of the metal complex includetris(8-quinolinolato)aluminum (III) (Alq),tris(4-methyl-8-quinolinolato)aluminum (Almq₃),bis(10-hydroxybenzo[h]quinolinato)beryllium (BeBq₂),bis(2-methyl-8-quinolinato) (4-phenylphenolato)aluminum (III)(BAlq),bis(8-quinolinato)zinc(II) (Znq),bis[2-(2-benzoxazolyl)phenolato]zinc(II) (ZnPBO), andbis[2-(2-benzothiazolyl)phenolato]zinc(II)(ZnBTZ). Examples of theheteroaromatic compound include2-(4-biphenylyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (PBD),1,3-bis[5-(ptert-butylphenyl)-1,3,4-oxadiazole-2-yl]benzene (OXD-7),3-(4-tert-butylphenyl)-4-phenyl-5-(4-biphenylyl)-1,2,4-triazole (TAZ),3-(4-tert-butylphenyl)-4-(4-ethylphenyl)-5-(4-biphenylyl)-1,2,4-triazole(p-EtTAZ), bathophenanthroline (BPhen), bathocuproine (BCP), and4,4′-bis(5-methylbenzoxazole-2-yl)stilbene (BzOs). The above compoundshave an electron mobility of mainly 10⁻⁶ cm²/Vs or more. Examples of themacromolecular compound includepoly[(9,9-dihexylfluorene-2,7-diyl)-co-(pyridine-3,5-diyl)] (PF-Py), andpoly[(9,9-dioctylfluorene-2,7-diyl)-co-(2,2′-bipyridine-6,6′-diyl)](PF-BPy).

Other materials are also usable in the electron transporting layer iftheir electron transporting ability is higher than their holetransporting ability. The electron transporting layer may be a singlelayer or a laminate of two or more layers each comprising the materialmentioned above.

Electron Injecting Layer

The electron injecting layer comprises a highly electron-injectingmaterial, for example, an alkali metal, an alkaline earth metal, and acompound of these metals, such as lithium (Li), cesium (Cs), calcium(Ca), lithium fluoride (LiF), cesium fluoride (CsF), calcium fluoride(CaF2), and lithium oxide (LiOx). In addition, an electron transportingmaterial which is doped with an alkali metal, an alkaline earth metal ora compound thereof, for example, Alq doped with magnesium (Mg), is alsousable. By using such a material, electrons are efficiently injectedfrom the cathode.

A composite material obtained by mixing an organic compound and anelectron donor is also usable in the electron injecting layer. Such acomposite material is excellent in the electron injecting ability andthe electron transporting ability, because the organic compound receiveselectrons from the electron donor. The organic compound is preferably amaterial excellent in transporting the received electrons. Examplesthereof are the materials for the electron transporting layer mentionedabove, such as the metal complex and the aromatic heterocyclic compound.Any material capable of giving its electron to another organic compoundis usable as the electron donor. Preferred examples thereof are analkali metal, an alkaline earth metal, and a rare earth metal, such aslithium, cesium, magnesium, calcium, erbium, and ytterbium; an alkalimetal oxide and an alkaline earth metal oxide, such as, lithium oxide,calcium oxide, and barium oxide; a Lewis base, such as magnesium oxide;and an organic compound, such as tetrathiafulvalene (TTF).

Cathode

The cathode is formed preferably from a metal, an alloy, an electricallyconductive compound, or a mixture thereof, each having a small workfunction, for example, a work function of 3.8 eV or less. Examples ofthe material for the cathode include a metal of the group 1 or 2 of theperiodic table, for example, an alkali metal, such as lithium (Li) andcesium (Cs), an alkaline earth metal, such as magnesium (Mg), an alloycontaining these metals (for example, MgAg and AlLi), a rare earthmetal, such as europium (Eu) and ytterbium (Yb), and an alloy containinga rare earth metal.

The alkali metal, the alkaline earth metal, and the alloy thereof can bemade into the cathode by a vacuum vapor deposition or a sputteringmethod. When a silver paste, etc. is used, a coating method and aninkjet method are usable.

When the electron injecting layer is formed, the material for thecathode can be selected independently from the work function and variouselectroconductive materials, such as Al, Ag, ITO, graphene, and indiumoxide-tin oxide doped with silicon or silicon oxide, are usable. Theseelectroconductive materials are made into films by a sputtering method,an inkjet method, and a spin coating method.

Each layer of the organic EL device in an aspect of the invention can beformed by a known method, such as a vapor deposition method and acoating method. For example, each layer can be formed by a known vapordeposition method, such as a vacuum vapor deposition method and amolecular beam evaporation method (MBE method), and a known coatingmethod using a solution of the compound for forming the layer, such as adipping method, a spin coating method, a casting method, a bar coatingmethod, and a roll coating method.

The thickness of each organic thin film layer is not particularlylimited and preferably several nanometers to 1 μm, because anexcessively small thickness may cause defects such as pin holes and anexcessively large thickness may require a high driving voltage.

In an aspect of the invention, the organic electroluminescence devicecan be used in an electronic device, for example, as display parts, suchas organic EL panel module, display devices of television sets, mobilephones, personal computer, etc., and light emitting sources of lightingequipment and vehicle lighting equipment.

EXAMPLES

The invention will be described in more detail with reference to theexamples and comparative examples. It should be noted that the scope ofthe invention is not limited to the following examples.

Synthesis Example 1: Synthesis of Intermediate 2

The intermediate 1 (24 g) synthesized by the method described in JP2009-057323A was dissolved in dimethylformamide (500 mL), and sodiumborohydride (12 g) and aluminum chloride (40 g) were added to theresultant solution little by little under cooling with ice. Afterstirring the mixture at room temperature for 2 h, a 1 M aqueous solutionof sodium hydroxide was added under cooling with ice. The obtainedmixture was filtered through Celite. The filtrate was washed with asaturated brine and then extracted with dichloromethane. The solvent wasevaporated off under reduced pressure. The obtained residue was purifiedby a silica gel column chromatography to obtain the intermediate 2 (21.4g, 89% yield).

Synthesis Example 2: Synthesis of Intermediate 3

The intermediate 2 (21 g) obtained in Synthesis Example 2 was dissolvedin tetrahydrofuran (500 mL), and triethylamine (18 g) was added to theresultant solution. The obtained mixture was stirred for 2 h whileadding acetyl chloride (16 g) dropwise under cooling with ice. Afteradding water under cooling with ice, the mixture was washed with asaturated brine and then extracted with dichloromethane. The solvent wasevaporated off under reduced pressure. The obtained residue was purifiedby a silica gel column chromatography to obtain the intermediate 3 (21.7g, 90% yield).

Synthesis Example 3: Synthesis of Intermediate 4

Under argon atmosphere, the intermediate 3 (21 g) obtained in SynthesisExample 2 was dissolved in ethanol (1 L), and a 10% palladium/carbon (10g) was added to the resultant solution. After replacing the atmospherewith hydrogen gas, the mixture was vigorously stirred at roomtemperature for 8 h. The reaction mixture was filtered through Celiteand the solvent was evaporated off under reduced pressure. The obtainedresidue was purified by a silica gel column chromatography to obtain theintermediate 4 (11.9 g, 69% yield).

Synthesis Example 4: Synthesis of Intermediate 5

The intermediate 4 (11 g) obtained in Synthesis Example 3 was dissolvedin dimethylsulfoxide (500 mL). After adding potassium t-butoxide (28 g)to the resultant solution under cooling with ice, methyl iodide (36 g)was added dropwise. After stirring at room temperature for 6 h, anaqueous solution of ammonium chloride was added under cooling with ice.The obtained mixture was extracted with dichloromethane and the solventwas evaporated off under reduced pressure. The obtained residue waspurified by a silica gel column chromatography to obtain theintermediate 5 (8.8 g, 72% yield).

Synthesis Example 5: Synthesis of Intermediate 6

The intermediate 5 (150 mg) obtained in Synthesis Example 4 wasdissolved in dimethylformamide (15 mL), and N-bromosuccinimide (181 mg)was added to the resultant solution at room temperature. After stirringat room temperature for one hour, the residue was purified by a silicagel column chromatography to obtain the intermediate 6 (146 mg, 77%yield).

Synthesis Example 6: Synthesis of Intermediate 10

Under argon atmosphere, a mixture of aniline (27.3 L), the intermediate6 (56.0 mg), tris(dibenzylideneacetone)dipalladium(0) (11.0 mg),tri-t-butylphosphonium tetrafluoroborate (7.0 mg), and sodium t-butoxide(43.3 mg) in dehydrated xylene (1 mL) was stirred for 9 h whilerefluxing under heating. After cooling to room temperature, the solventwas evaporated off. The obtained residue was purified by a silica gelcolumn chromatography to obtain the intermediate 10 (40 mg, 70% yield).

Example 1: Synthesis of Compound 1

Under argon atmosphere, a mixture of the intermediate 6 (40 mg), theintermediate 10 (42.9 mg), tris(dibenzylideneacetone)dipalladium(0)(5.50 mg), tri-t-butylphosphonium tetrafluoroborate (3.5 mg), and sodiumt-butoxide (29.8 mg) in dehydrated xylene (1 mL) was stirred for 7 hwhile refluxing under heating. After cooling to room temperature, thesolvent was evaporated off. The obtained residue was purified by asilica gel column chromatography to obtain the compound 1 as a solid (20mg, 28% yield). The obtained compound was identified by a massspectrography which showed m/e=677 to the molecular weight of 677.31.

Example 2: Synthesis of Compound 2

The compound 2 was synthesized according to the following scheme.

(2-1) Synthesis of 2-bromo-3-methylnaphthalene

Under argon atmosphere, 2,3-dibromonaphthalene (10.0 g),[1,1′-bis(diphenylphosphino)ferrocene]palladium(II) dichloridedichloromethane adduct (0.572 g), and toluene (300 mL) were charged in aflask. A 0.92 M tetrahydrofuran solution of methylmagnesium bromide (38mL) was added to the resultant mixture under stirring and then themixture was stirred for 2.5 h while refluxing under heating. Aftercooling to room temperature, water and ethyl acetate were added and theorganic layer was collected. The organic layer was concentrated and theresidue was purified by a silica gel column chromatography to obtain awhite solid (6.04 g, 78% yield). The result of mass spectrometricanalysis (m/e=221 to the molecular weight of 221.1) showed that theobtained compound was the target 2-bromo-3-methylnaphthalene.

(2-2) Synthesis of Intermediate 7

To 2-bromo-3-methylnaphthalene (4.00 g) in a flask,bis(pinacolato)diboron (5.5 g),[1,1′-bis(diphenylphosphino)ferrocene]palladium(II) dichloridedichloromethane adduct (0.443 g), and dioxane (90 mL) were added. Underargon atmosphere, the resultant mixture was stirred at 100° C. for 8 hunder heating. After cooling to room temperature, a saturated aqueoussolution of ammonium chloride and ethyl acetate were added, and theproduct was extracted into the organic layer. The collected organiclayer was concentrated and the residue was purified by a silica gelcolumn chromatography to obtain a white solid (3.81 g, 79% yield). Theresult of mass spectrometric analysis (m/e=268 to the molecular weightof 268.16) showed that the product was the target intermediate 7.

(2-3) Synthesis of Intermediate 8

Under argon atmosphere, 2-chloro-3-iodonaphthalene (2.13 g), theintermediate 7 (2.08 g), tetrakistriphenylphosphine palladium (0.17 g),sodium carbonate (2.35 g), dimethoxyethane (60 mL), and water (15 mL)were charged in a flask. The mixture was stirred at 80° C. for 7 h underheating. After cooling to room temperature, water and ethyl acetate wereadded and then the organic layer was collected. The collected organiclayer was concentrated and the residue was purified by a silica gelcolumn chromatography to obtain a white solid (1.52 g, 63% yield). Theresult of mass spectrometric analysis (m/e=302 to the molecular weightof 302.80) showed that the product was the target intermediate 8.

(2-4) Synthesis of Intermediate 4

Under argon atmosphere, the intermediate 8 (1.52 g), palladium(II)acetate (0.023 g), 1,3-bis(2,6-diisopropylphenyl)imidazolium chloride(0.085 g), potassium carbonate (0.694 g), and N-methylpyrrolidone (15mL) were charged in a flask. The mixture was stirred at 150° C. for 8 hwhile refluxing under heating. After cooling to room temperature,methanol was added and then the precipitate was collected by filtration.The collected solid was purified by a silica gel column chromatographyto obtain a white solid (0.83 g, 62% yield). The result of massspectrometric analysis (m/e=266 to the molecular weight of 266.34)showed that the product was the target intermediate 4.

(2-5) Synthesis of Intermediate 6

The intermediate 6 was obtained in the same manner as in SynthesisExample 4 and Synthesis Example 5.

(2-6) Synthesis of Intermediate 9

Under argon atmosphere, the intermediate 6 (0.38 g),tris(dibenzylideneacetone)dipalladium (0.018 g),2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (SPhos) (0.033 g),sodium t-butoxide (0.134 g), and toluene (5 mL) were charged in a flask.After adding 4-t-butylaniline (0.31 mL), the resultant mixture wasstirred at 100° C. for 6 h under heating. The reaction solution wascooled to room temperature and then purified by a silica gel columnchromatography to obtain a yellow solid (0.33 g, 74% yield). The resultof mass spectrometric analysis (m/e=441 to the molecular weight of441.60) showed that the product was the target intermediate 9.

(2-7) Synthesis of Compound 2

Under argon atmosphere, the intermediate 9 (0.26 g), the intermediate 6(0.22 g), tris(dibenzylideneacetone)dipalladium (0.011 g),tri-t-butylphosphonium tetrafluoroborate (0.014 g), sodium t-butoxide(0.113 g), and xylene (3 mL) were charged in a flask. The resultantmixture was stirred at 100° C. for 3 h under heating. The reactionsolution was purified by a silica gel column chromatography and theobtained solid was washed with methanol to obtain a yellow solid (0.21g, 49% solid). The result of mass spectrometric analysis (m/e=734 to themolecular weight of 733.98) showed that the product was the targetcompound 2.

Measurement of Emission Spectrum

A toluene solution of the compound 1 (10⁻⁵ mol/L) was used as ameasuring sample. The emission spectrum of the sample was measured byusing a fluorescence spectrophotometer F-7100 manufactured by HitachiHigh-Technologies Corporation at a normal temperature (300 K). Theresult is shown in FIG. 2. The emission spectrum of the compound 2 wasmeasured in the same manner. The result is shown in FIG. 3.

Comparative Examples 1 and 2

The emission spectrum of each of the following comparative compounds 1and 2 was measured in the same manner as above. The results are shown inFIGS. 4 and 5.

As seen from the emission spectra of FIGS. 2 to 5, each emissionspectrum of the compounds 1 and 2 of the invention has an emission peakin the wavelength region suitable for a blue emitting device. Theemission peak has a narrow half width and has no second peak, i.e., is asingle peak. Therefore, a blue emitting organic EL device with a highcolor purity is obtained by using the compound of the invention whichcomprises a specific main skeleton, i.e., a fused fluorene structure, asa dopant material for the light emitting layer.

Example 3

Production of Organic EL Device

A glass substrate of 25 mm×75 mm×1.1 mm thickness having ITO transparentelectrode (anode) (product of Geomatec Company) was cleaned byultrasonic cleaning in isopropyl alcohol for 5 min and then UV ozonecleaning for 30 min.

The cleaned glass substrate having the transparent electrode lines wasmounted to a substrate holder of a vacuum vapor deposition apparatus.The compound HI-1 was vapor-deposited on the surface on which thetransparent electrode line was formed so as to cover the transparentelectrode, thereby forming an HI-1 film of 10 nm thick. The HI-1 filmworks as a hole injecting layer.

Successively after forming the HI-1 film, the compound HT-1 was vapordeposited to form an HT-1 film of 80 nm thick on the HI-1 film. The HT-1film works as a first hole transporting layer.

Successively after forming the HT-1 film, the compound HT-2 was vapordeposited to form an HT-2 film of 10 nm thick on the HT-1 film. The HT-2film works as a second hole transporting layer.

On the HT-2 film, the compound BH-1 (host material) and the compound 2(dopant material) were vapor co-deposited to form a light emitting layerof 25 nm thick. The concentration or the compound 2 was 4% by weight.

On the light emitting layer, the compounds ET-1 and the compound ET-2were vapor deposited in a weight ratio of 1:1 to form an electrontransporting layer of 25 nm thick.

On the electron transporting layer, the compound ET-2 was vapordeposited to form an electron injecting layer of 1 nm thick.

Then, a metallic Al was vapor deposited on the ET-2 layer to form ametal cathode of 80 nm thick.

The organic EL device was thus produced.

Evaluation of Organic EL Device

The emission spectrum of the organic EL device thus produced was measureby using a spectroradiometer “CS-1000” (manufactured by Konica Minolta,Inc.) by applying a voltage to the device so as to regulate the currentdensity to 10 mA/cm². The result is shown in FIG. 6, wherein the maximumintensity of the measured spectroradiometric spectrum is taken as 1.0.The chromaticity of the light emitted from the device is shown in Table1.

Comparative Example 3

An organic EL device was produced in the same manner as in Example 3except for using the comparative compound 3 in place of the compound 2.The device was evaluated in the same manner as in Example 3, the resultsof which are shown in FIG. 7 and Table 1.

TABLE 1 Chromaticity CIEx CIEy Example 3 Compound 2 0.140 0.094Comparative Comparative 0.143 0.110 Example 3 compound 3

As compared with the emission spectrum of FIG. 7 for the EL device usingthe comparative compound 3, it can be found that the emission spectrumof FIG. 6 for the EL device using the compound 2 of the invention is asingle peak spectrum having no second peak. This means that the emissioncomponent of the longer wavelength side is reduced in the emission fromthe EL device of the invention. As seen from Table 1, the CIEy value ofthe device using the compound of the invention is smaller, showing thata deeper blue emission with a good chromaticity is obtained.

Thus, the compound of the invention realizes an organic EL device with agood color purity, and therefore, is advantageous for optical design.

REFERENCE SIGNS LIST

-   1: Organic EL device-   2: Substrate-   3: Anode-   4: Cathode-   5: Light emitting layer-   6: Anode-side organic thin film layer-   7: Cathode-side organic thin film layer-   10: Emission unit

The invention claimed is:
 1. A compound represented by the formula (1):

wherein: Ar is a substituted or unsubstituted alkyl group having 1 to 20carbon atoms, a substituted or unsubstituted aryl group having 6 to 30ring carbon atoms, or a substituted or unsubstituted nitrogen-comprisingheteroaryl group having 5 to 30 ring atoms; each of L₁ and L₂ isindependently a single bond, a substituted or unsubstituted arylenegroup having 6 to 30 ring carbon atoms, a substituted or unsubstitutedheteroarylene group having 5 to 30 ring atoms, or a substituted orunsubstituted divalent linking group wherein 2 to 4 groups selected froman arylene group having 6 to 30 ring carbon atoms and a heteroarylenegroup having 5 to 30 ring atoms are bonded to each other via a singlebond; A is a monovalent group represented by the formula (2):

wherein: each of R₁ and R₂ is independently a hydrogen atom, asubstituted or unsubstituted alkyl group having 1 to 20 carbon atoms, amono-, di-, or trialkylsilyl group each comprising a substituted orunsubstituted alkyl group having 1 to 20 carbon atoms, a substituted orunsubstituted aryl group having 6 to 30 ring carbon atoms, a mono-, di-,or triarylsilyl group each comprising a substituted or unsubstitutedaryl group having 6 to 30 ring carbon atoms, or a substituted orunsubstituted heteroaryl group having 5 to 30 ring atoms, wherein R₁ andR₂ may be bonded to each other to form a ring; adjacent two groups inone pair selected from R₃ and R₄, R₄ and R₅, and R₅ and R₆ are bonded toeach other to form a divalent group represented by the formula (3);adjacent two groups in one pair selected from R₇ and R₈, R₈ and R₉, andR₉ and R₁₀ are bonded to each other to form a divalent group representedby the formula (4);

wherein: each of R₁₁ to R₁₈ is independently a hydrogen atom, asubstituted or unsubstituted alkyl group having 1 to 20 carbon atoms, amono-, di-, or trialkylsilyl group each comprising a substituted orunsubstituted alkyl group having 1 to 20 carbon atoms, a substituted orunsubstituted aryl group having 6 to 30 ring carbon atoms, a mono-, di-,or triarylsilyl group each comprising a substituted or unsubstitutedaryl group having 6 to 30 ring carbon atoms, or a substituted orunsubstituted heteroaryl group having 5 to 30 ring atoms; provided thatone selected from R₃ to R₆ which do not form the divalent grouprepresented by formula (3), R₇ to R₁₀ which do not form the divalentgroup represented by the formula (4), and R₁₁ to R₁₈ is a single bondbonded to L₁; each selected from R₃ to R₆ which do not form the divalentgroup represented by the formula (3) and is not a single bond bonded toL₁, and each selected from R₇ to R₁₀ which do not form the divalentgroup represented by the formula (4) and is not a single bond bonded toL₁ is independently a hydrogen atom, a substituted or unsubstitutedalkyl group having 1 to 20 carbon atoms, a mono-, di-, or trialkylsilylgroup each comprising a substituted or unsubstituted alkyl group having1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6to 30 ring carbon atoms, a mono-, di-, or triarylsilyl group eachcomprising a substituted or unsubstituted aryl group having 6 to 30 ringcarbon atoms, or a substituted or unsubstituted heteroaryl group having5 to 30 ring atoms; B is a monovalent group represented by the formula(5):

wherein: each of R₂₁ and R₂₂ is independently a hydrogen atom, asubstituted or unsubstituted alkyl group having 1 to 20 carbon atoms, amono-, di-, or trialkylsilyl group each comprising a substituted orunsubstituted alkyl group having 1 to 20 carbon atoms, a substituted orunsubstituted aryl group having 6 to 30 ring carbon atoms, a mono-, di-,or triarylsilyl group each comprising a substituted or unsubstitutedaryl group having 6 to 30 ring carbon atoms, or a substituted orunsubstituted heteroaryl group having 5 to 30 ring atoms, wherein R₂₁and R₂₂ may be bonded to each other to form a ring; each of R₂₃ to R₃₀is independently a hydrogen atom, a substituted or unsubstituted alkylgroup having 1 to 20 carbon atoms, a mono-, di-, or trialkylsilyl groupeach comprising a substituted or unsubstituted alkyl group having 1 to20 carbon atoms, a substituted or unsubstituted aryl group having 6 to30 ring carbon atoms, a mono-, di-, or triarylsilyl group eachcomprising a substituted or unsubstituted aryl group having 6 to 30 ringcarbon atoms, or a substituted or unsubstituted heteroaryl group having5 to 30 ring atoms; adjacent groups in at least one pair selected fromthe group consisting of R₂₃ and R₂₄, R₂₄ and R₂₅, R₂₅ and R₂₆ are bondedto each other to form a ring; or adjacent groups in at least one pairselected from the group consisting of R₂₇ and R₂₈, R₂₈ and R₂₉, and R₂₉and R₃₀ are bonded to each other to form a carbon ring; provided thatone selected from R₂₇ to R₃₀ which do not form a carbon ring is a singlebond bonded to L₂, or one of ring carbon atoms of the carbon ring whichis formed by the at least one pair selected from the group consisting ofR₂₇ and R₂₈, R₂₈ and R₂₉, and R₂₉ and R₃₀ is bonded to L₂.
 2. Thecompound according to claim 1, wherein A is a monovalent grouprepresented by any of the formulae (6) to (11):

wherein R₁, R₂, R₅ to R₈, and R₁₁ to R₁₈ of the formula (6); R₁, R₂, R₅,R₆, and R₉ to R₁₈ of the formula (7); R₁ to R₄, R₉, R₁₀, and R₁₁ to R₁₈of the formula (8); R₁ to R₃, R₆, R₇, and R₁₀ to R₁₈ of the formula (9);R₁, R₂, R₅ to R₇, and R₁₀ to R₁₈ of the formula (10); and R₁ to R₄, R₇,and R₁₀ to R₁₈ of the formula (11) are independently as defined above.3. The compound according to claim 1, wherein one or two pairs selectedfrom R₂₃ and R₂₄, R₂₄ and R₂₅, and R₂₅ and R₂₆ of the formula (5) form adivalent group represented by the formula (12) or (13), and one or twopairs selected from R₂₇ and R₂₈, R₂₈ and R₂₉, and R₂₉ and R₃₀ of formula(5) form a divalent group represented by the formula (14):

wherein: each of R₃₁ to R₃₄ of the formula (12), R₃₅ to R₃₈ of theformula (13), and R₃₉ to R₄₂ of the formula (14) is independently ahydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20carbon atoms, a mono-, di-, or trialkylsilyl group each comprising asubstituted or unsubstituted alkyl group having 1 to 20 carbon atoms, asubstituted or unsubstituted aryl group having 6 to 30 ring carbonatoms, a mono-, di-, or triarylsilyl group each comprising a substitutedor unsubstituted aryl group having 6 to 30 ring carbon atoms, or asubstituted or unsubstituted heteroaryl group having 5 to 30 ring atoms;adjacent two groups each selected from the group consisting of R₃₁ toR₃₄, R₃₅ to R₃₈, and R₃₉ to R₄₂ may be bonded to each other to form aring; one of R₃₉ to R₄₂ may be a single bond which is bonded to L₂; X isCR₄₃R₄₄, NR₄₅, O, or S; each of R₄₃ to R₄₅ is independently a hydrogenatom, a substituted or unsubstituted alkyl group having 1 to 20 carbonatoms, a mono-, di-, or trialkylsilyl group each comprising asubstituted or unsubstituted alkyl group having 1 to 20 carbon atoms, asubstituted or unsubstituted aryl group having 6 to 30 ring carbonatoms, a mono-, di-, or triarylsilyl group each comprising a substitutedor unsubstituted aryl group having 6 to 30 ring carbon atoms, or asubstituted or unsubstituted heteroaryl group having 5 to 30 ring atoms;and R₄₃ and R₄₄ may be bonded to each other to form a ring.
 4. Thecompound according to claim 1, wherein B is a monovalent grouprepresented by any of the formulae (15) to (23):

wherein: R₂₁, R₂₂, and R₂₅ to R₂₈ of the formula (15), R₂₁, R₂₂, R₂₅,R₂₆, R₂₉, and R₃₀ of the formula (16), R₂₁ to R₂₄, R₂₇, and R₂₈ of theformula (17), R₂₁ to R₂₄, R₂₉, and R₃₀ of the formula (18), R₂₁ to R₂₃,R₂₆, R₂₇, and R₃₀ of the formula (19), R₂₁, R₂₂, R₂₅ to R₂₇, and R₃₀ ofthe formula (20), R₂₁ to R₂₃, and R₂₆ to R₂₈ of the formula (21), R₂₁ toR₂₄, R₂₇, and R₃₀ of formula (22), and R₂₁ to R₂₃, R₂₆, R₂₉, and R₃₀ ofthe formula (23) are independently as defined above; each of R₃₁ to R₃₄and R₃₉ to R₄₂ of the formulae (15) to (23) is independently a hydrogenatom, a substituted or unsubstituted alkyl group having 1 to 20 carbonatoms, a mono-, di-, or trialkylsilyl group each comprising asubstituted or unsubstituted alkyl group having 1 to 20 carbon atoms, asubstituted or unsubstituted aryl group having 6 to 30 ring carbonatoms, a mono-, di-, or triarylsilyl group each comprising a substitutedor unsubstituted aryl group having 6 to 30 ring carbon atoms, or asubstituted or unsubstituted heteroaryl group having 5 to 30 ring atoms;adjacent two groups each selected from R₃₁ to R₃₄ and R₃₉ to R₄₂ may bebonded to each other to form a ring; and one of R₃₉ to R₄₂ may be asingle bond which is bonded to L₂.
 5. The compound according to claim 1,wherein B is represented by the formula (24) or (25):

wherein: R₂₂, R₂₇ to R₃₀ of the formula (24) and R₂₁ to R₂₆ of theformula (25) are independently as defined above; each of R₃₁ to R₃₄ ofthe formula (24) and R₃₉ to R₄₂ of the formula (25) is independently ahydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20carbon atoms, a mono-, di-, or trialkylsilyl group each comprising asubstituted or unsubstituted alkyl group having 1 to 20 carbon atoms, asubstituted or unsubstituted aryl group having 6 to 30 ring carbonatoms, a mono-, di-, or triarylsilyl group each comprising a substitutedor unsubstituted aryl group having 6 to 30 ring carbon atoms, or asubstituted or unsubstituted heteroaryl group having 5 to 30 ring atoms;adjacent two groups each selected from R₃₁ to R₃₄ and R₃₉ to R₄₂ may bebonded to each other to form a ring; one of R₃₉ to R₄₂ may be a singlebond which is bonded to L₂; and two groups R₃₁, two groups R₃₂, twogroups R₃₃, and two groups R₃₄ each in the formula (24), and two groupsR₃₉, two groups R₄₀, two groups R₄₁, and two groups R₄₂ each in theformula (25) may be the same or different, respectively.
 6. The compoundaccording to claim 1, wherein B is a monovalent group represented by anyof the formulae (26) to (38):

wherein: R₂₁ to R₂₃ and R₂₆ to R₃₀ of the formulae (26) and (31) to(38), R₂₃ to R₃₀ of the formula (27), R₂₁ to R₂₄ and R₂₇ to R₃₀ of theformula (28), R₂₁ to R₂₆, R₂₉, and R₃₀ of the formula (29), and R₂₁ toR₃₀ of the formula (30) are independently as defined above; each of R₃₅to R₃₈ of the formula (26), R₃₁ to R₃₄ of the formula (28), R₃₉ to R₄₂of the formula (29), R₃₅ and R₃₆ of the formula (31), and R₃₅ to R₃₈ ofthe formulae (32) to (38) is independently a hydrogen atom, asubstituted or unsubstituted alkyl group having 1 to 20 carbon atoms, amono-, di-, or trialkylsilyl group each comprising a substituted orunsubstituted alkyl group having 1 to 20 carbon atoms, a substituted orunsubstituted aryl group having 6 to 30 ring carbon atoms, a mono-, di-,or triarylsilyl group each comprising a substituted or unsubstitutedaryl group having 6 to 30 ring carbon atoms, or a substituted orunsubstituted heteroaryl group having 5 to 30 ring atoms; adjacent twogroups each selected from R₃₁ to R₃₄, R₃₅ to R₃₈, and R₃₉ to R₄₂ may bebonded to each other to form a ring; one of R₃₉ to R₄₂ may be a singlebond which is bonded to L₂; each of R₄₃ and R₄₄ of the formulae (26),(31), and (38) and R₄₅ of the formulae (34) and (37) is independently ahydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20carbon atoms, a mono-, di-, or trialkylsilyl group each comprising asubstituted or unsubstituted alkyl group having 1 to 20 carbon atoms, asubstituted or unsubstituted aryl group having 6 to 30 ring carbonatoms, a mono-, di-, or triarylsilyl group each comprising a substitutedor unsubstituted aryl group having 6 to 30 ring carbon atoms, or asubstituted or unsubstituted heteroaryl group having 5 to 30 ring atoms;and R₄₃ and R₄₄ may be bonded to each other to form a ring.
 7. Thecompound according to claim 1, wherein Ar is represented by the formula(5).
 8. The compound according to claim 7, wherein B and Ar are thesame.
 9. The compound according to claim 1, wherein A and B are thesame.
 10. The compound according to claim 9, wherein A is represented byany of the formulae (6) to (11):

wherein R₁, R₂, R₅ to R₈, and R₁₁ to R₁₈ of the formula (6); R₁, R₂, R₅,R₆, and R₉ to R₁₈ of the formula (7); R₁ to R₄, R₉, R₁₀, and R₁₁ to R₁₈of the formula (8); R₁ to R₃, R₆, R₇ and R₁₀ to R₁₈ of the formula (9);R₁, R₂, R₅ to R₇ and R₁₀ to R₁₈ of the formula (10); and R₁ to R₄, R₇and R₁₀ to R₁₈ of the formula (11) are independently as defined above;and B is represented by any of the formulae (15) to (23):

wherein: R₂₁, R₂₂, and R₂₅ to R₂₈ of the formula (15), R₂₁, R₂₂, R₂₅,R₂₆, R₂₉ and R₃₀ of the formula (16), R₂₁ to R₂₄, R₂₇, and R₂₈ of theformula (17), R₂₁ to R₂₄, R₂₉ and R₃₀ of the formula (18), R₂₁ to R₂₃,R₂₆, R₂₇ and R₃₀ of the formula (19), R₂₁, R₂₂, R₂₅ to R₂₇, and R₃₀ ofthe formula (20), R₂₁ to R₂₃, and R₂₆ to R₂₈ of the formula (21), R₂₁ toR₂₄, R₂₇, and R₃₀ of formula (22), and R₂₁ to R₂₃, R₂₆, R₂₉ and R₃₀ ofthe formula (23) are independently as defined above; each of R₃₁ to R₃₄and R₃₉ to R₄₂ of the formulae (15) to (23) is independently a hydrogenatom a substituted or unsubstituted alkyl group having 1 to 20 carbonatoms, a mono-, di-, or trialkylsilyl group each comprising asubstituted or unsubstituted alkyl group having 1 to 20 carbon atoms, asubstituted or unsubstituted aryl group having 6 to 30 ring carbonatoms, a mono-, di-, or triarylsilyl group each comprising a substitutedor unsubstituted aryl group having 6 to 30 ring carbon atoms, or asubstituted or unsubstituted heteroaryl group having 5 to 30 ring atoms;adjacent two groups each selected from R₃₁ to R₃₄ and R₃₉ to R₄₂ may bebonded to each other to form a ring; and one of R₃₉ to R₄₂ may be asingle bond which is bonded to L₂.
 11. The compound according to claim1, wherein A, B, and Ar are the same.
 12. The compound according toclaim 11, wherein A is represented by any of the formulae (6) to (11):

wherein R₁, R₂, R₅ to R₈, and R₁₁ to R₁₈ of the formula (6); R₁, R₂, R₅,R₆, and R₉ to R₁₈ of the formula (7); R₁ to R₄, R₉, R₁₀ and R₁₁ to R₁₈of the formula (8); R₁ to R₃, R₆, R₇, and R₁₀ to R₁₈ of the formula (9);R₁, R₂, R₅ to R₇ and R₁₀ to R₁₈ of the formula (10); and R₁ to R₄, R₇,and R₁₀ to R₁₈ of the formula (11) are independently as defined above; Bis represented by any of the formulae (15) to (23):

wherein: R₂₁, R₂₂, and R₂₅ to R₂₈ of the formula (15), R₂₁, R₂₂, R₂₅,R₂₆, R₂₉, and R₃₀ of the formula (16), R₂₁ to R₂₄, R₂₇, and R₂₈ of theformula (17), R₂₁ to R₂₄, R₂₉ and R₃₀ of the formula (18), R₂₁ to R₂₃,R₂₆, R₂₇, and R₃₀ of the formula (19), R₂₁, R₂₂, R₂₅ to R₂₇, and R₃₀ ofthe formula (20), R₂₁ to R₂₃, and R₂₆ to R₂₈ of the formula (21), R₂₁ toR₂₄, R₂₇, and R₃₀ of formula (22), and R₂₁ to R₂₃, R₂₆, R₂₉, and R₃₀ ofthe formula (23) are independently as defined above; each of R₃₁ to R₃₄and R₃₉ to R₄₂ of the formulae (15) to (23) is independently a hydrogenatom, a substituted or unsubstituted alkyl group having 1 to 20 carbonatoms, a mono-, di-, or trialkylsilyl group each comprising asubstituted or unsubstituted alkyl group having 1 to 20 carbon atoms, asubstituted or unsubstituted aryl group having 6 to 30 ring carbonatoms, a mono-, di-, or triarylsilyl group each comprising a substitutedor unsubstituted aryl group having 6 to 30 ring carbon atoms, or asubstituted or unsubstituted heteroaryl group having 5 to 30 ring atoms;adjacent two groups each selected from R₃₁ to R₃₄ and R₃₉ to R₄₂ may bebonded to each other to form a ring; and one of R₃₉ to R₄₂ may be asingle bond which is bonded to L₂; and Ar is represented by any of theformulae (6) to (11).
 13. The compound according to claim 1, wherein L₁is a single bond.
 14. The compound according to claim 1, wherein L₂ is asingle bond.
 15. The compound according to claim 1, wherein Ar is asubstituted or unsubstituted aryl group having 6 to 30 ring carbonatoms.
 16. A material for organic electroluminescence device comprisingthe compound according to claim
 1. 17. An organic electroluminescencedevice comprising a cathode, an anode, and at least one organic thinfilm layer disposed between the cathode and the anode, wherein the atleast one organic thin film layer comprises a light emitting layer andat least one layer of the at least one organic thin film layer comprisesthe compound according to claim
 1. 18. The organic electroluminescencedevice according to claim 17, wherein the light emitting layer comprisesthe compound.
 19. The organic electroluminescence device according toclaim 18, wherein the compound is a dopant.
 20. An electronic devicecomprising the organic electroluminescence device according to claim 17.